tag:blogger.com,1999:blog-53140386508120936452024-03-13T03:33:54.858+05:30Organic Synthesis InternationalOrganic Synthesis International by Dr Anthony Melvin Crasto Ph.D, Worlddrugtracker, Million hits on google on all sites, One lakh connections worldwide. Pushing boundaries.Interaction site for Organic chemists worldwide, Mail me at amcrasto@gmail.com if you like meDRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.comBlogger339125tag:blogger.com,1999:blog-5314038650812093645.post-51752064464105381402019-02-01T19:19:00.001+05:302019-02-01T19:19:07.992+05:30Design, synthesis and antimicrobial activity of usnic acid derivatives<div dir="ltr" style="text-align: left;" trbidi="on">
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Design, synthesis and antimicrobial activity of usnic acid derivatives</h2>
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<span class="article__author-link" style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><a href="https://pubs.rsc.org/en/results?searchtext=Author%3AVictor%20Kartsev" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Victor Kartsev</a>,<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">a</span> </span><span class="article__author-link" style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><a href="https://pubs.rsc.org/en/results?searchtext=Author%3ABoris%20Lichitsky" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Boris Lichitsky</a>,<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">b</span> </span><span class="article__author-link" style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><a href="https://pubs.rsc.org/en/results?searchtext=Author%3AAthina%20Geronikaki" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Athina Geronikaki</a>,*<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">c</span> </span><span class="article__author-link" style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><a href="https://pubs.rsc.org/en/results?searchtext=Author%3AAnthi%20Petrou" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Anthi Petrou</a>,<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">c</span> </span><span class="article__author-link" style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><a href="https://pubs.rsc.org/en/results?searchtext=Author%3AMarija%20Smiljkovic" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Marija Smiljkovic</a>,<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">d</span> </span><span class="article__author-link" style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><a href="https://pubs.rsc.org/en/results?searchtext=Author%3AMarina%20Kostic" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Marina Kostic</a>,<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">d</span> </span><span class="article__author-link" style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><a href="https://pubs.rsc.org/en/results?searchtext=Author%3AOliver%20Radanovic" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Oliver Radanovic</a><span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">e</span> and </span><span class="article__author-link" style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><a href="https://pubs.rsc.org/en/results?searchtext=Author%3AMarina%20Sokovi%C4%87" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Marina Soković</a><span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">d</span> </span></div>
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*Corresponding authors</div>
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<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">a</span>InterBioscreen, Moscow, Russia</div>
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<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">b</span>Zelinsky Institute of Organic Chemistry, Leninsky Prospect, Moscow, Russia<br /><b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">E-mail:</b> <a href="mailto:blich2006@mail.ru" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;" title="blich2006@mail.ru">blich2006@mail.ru</a></div>
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<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">c</span>School of Health, Department of Pharmacy, Aristotle University of Thessaloniki, Greece</div>
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<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">d</span>Mycological Laboratory, Department of Plant Physiology, Institute for Biological Research, Siniša Stanković, University of Belgrade, Bulevar Despota Stefana 142, Belgrade, Serbia</div>
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<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">e</span>Scientific Institute of Veterinary Medicine of Serbia, ul. Vojvode Toze 14, 11000 Belgrade, Serbia</div>
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Abstract</h3>
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Usnic acid, a dibenzofuran, was originally isolated from lichens producing secondary metabolites, and is well known as an antibiotic, but is also endowed with several other interesting properties. Thus, the goal of this paper is the design of new usnic acid derivatives and evaluation of their antimicrobial activity. All newly synthesized compounds possess good antibacterial activity with MIC ranging from 1.02–50.93 × 10<small style="border: 0px; color: #555555; font-size: 12.528px; margin: 0px; outline: 0px; padding: 0px;"><span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">−2</span></small> mmol mL<small style="border: 0px; color: #555555; font-size: 12.528px; margin: 0px; outline: 0px; padding: 0px;"><span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">−1</span></small> and MBC from 2.05–70.57 × 10<small style="border: 0px; color: #555555; font-size: 12.528px; margin: 0px; outline: 0px; padding: 0px;"><span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">−2</span></small> mmol mL<small style="border: 0px; color: #555555; font-size: 12.528px; margin: 0px; outline: 0px; padding: 0px;"><span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">−1</span></small>. The most sensitive bacterial species was <em style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Staphylococcus aureus</em>, while <em style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Pseudomonas aeruginosa</em> and <em style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Escherichia coli</em> were the most resistant among the ATCC strains, and MRSA was the most resistant among all tested bacteria (ATCC and clinical isolates). Their antifungal activity was very strong (MIC = 0.35–7.53 × 10<small style="border: 0px; color: #555555; font-size: 12.528px; margin: 0px; outline: 0px; padding: 0px;"><span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">−2</span></small> mmol mL<small style="border: 0px; color: #555555; font-size: 12.528px; margin: 0px; outline: 0px; padding: 0px;"><span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">−1</span></small> and MFC = 0.70–15.05 × 10<small style="border: 0px; color: #555555; font-size: 12.528px; margin: 0px; outline: 0px; padding: 0px;"><span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">−2</span></small> mmol mL<small style="border: 0px; color: #555555; font-size: 12.528px; margin: 0px; outline: 0px; padding: 0px;"><span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">−1</span></small>) – better than those of reference compounds and usnic acid itself. The most sensitive fungal species was <em style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Trichoderma viride</em>, while <em style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Penicillium versicolor</em> var. <em style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">cyclopium</em> appeared to be the most resistant. It should be mentioned that in general most of the compounds showed weaker antibacterial activity, but better antifungal properties than usnic acid itself. The results allow us to conclude that the title compounds are good lead compounds for novel more active antibacterial drugs. On the other hand, these compounds are very promising as antifungals.</div>
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<a href="https://pubs.rsc.org/en/content/articlelanding/2018/md/c8md00076j#!divAbstract" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">https://pubs.rsc.org/en/content/articlelanding/2018/md/c8md00076j#!divAbstract</a></div>
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////////////<a href="https://pubs.rsc.org/en/content/articlelanding/2018/md/c8md00076j#!divAbstract" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Usnic acid, dibenzofuran</a></div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-40036136524236615062019-01-29T17:26:00.001+05:302019-01-29T17:26:49.722+05:30Large scale synthesis of chiral (3Z,5Z)-2,7-dihydro-1H-azepine-derived Hamari ligand for general asymmetric synthesis of tailor-made amino acids.<div dir="ltr" style="text-align: left;" trbidi="on">
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<a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2019/01/str3.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2019/01/str3.jpg" rel="attachment wp-att-10990"><img alt="str3" class="alignnone size-full wp-image-10990" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2019/01/str3.jpg" height="418" src="http://www.allfordrugs.com/wp-content/uploads/2019/01/str3.jpg" style="height: auto; max-width: 100%;" width="672" /></a> <a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2019/01/str4.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2019/01/str4.jpg" rel="attachment wp-att-10991"><img alt="str4" class="alignnone size-full wp-image-10991" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2019/01/str4.jpg" height="426" src="http://www.allfordrugs.com/wp-content/uploads/2019/01/str4.jpg" style="height: auto; max-width: 100%;" width="647" /></a></div>
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(<i>R</i>)-2,2′-bis(bromomethyl)-1,1′-binaphthalene ((<i>R</i>)-<b>17</b>) was prepared in the identical manner and had identical analytical properties to those given here.</div>
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<sup>1</sup>H NMR (400 MHz, CDCl<sub>3</sub>): <span data-mce-style="color: #ff0000;" style="color: red;">δ 4.25 (4H, s, 2 × CH<sub>2</sub>),</span> 7.07 (2H, dd, <i>J</i> = 8.4, 0.8 Hz, ArH), 7.27 (2H, ddd, <i>J</i> = 8.4, 6.8, 1.2 Hz, ArH), 7.48 (2H, ddd, <i>J</i> = 8.2, 6.8, 1.2 Hz, ArH), 7.74 (2H, d, <i>J</i> = 8.6 Hz, ArH), 7.92 (2H, d, <i>J</i> = 8.2 Hz, ArH), 8.02 (2H, d, <i>J</i> = 8.6 Hz, ArH).</div>
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<sup>13</sup>C NMR (100.6 MHz, CDCl<sub>3</sub>): <span data-mce-style="color: #ff0000;" style="color: red;">δ 32.6 (CH<sub>2</sub>)</span>, 126.80 (ArCH), 126.82 (ArCH), 126.84 (ArCH), 127.7 (ArCH), 128.0 (ArCH), 129.4 (ArCH), 132.5 (quaternary ArC), 133.3 (quaternary ArC), 134.1 (quaternary ArC), 134.2 (quaternary ArC).</div>
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[α]<sup>20</sup><sub>D</sub> = +173.8° (<i>c</i> = 1.0, CHCl<sub>3</sub>).</div>
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<a class="showFiguresEvent" data-mce-href="https://pubs.acs.org/doi/10.1021/acs.oprd.8b00406#" href="https://pubs.acs.org/doi/10.1021/acs.oprd.8b00406#" id="absImg" title="Open Figure Viewer"><img alt="Abstract Image" data-mce-src="https://pubs.acs.org/appl/literatum/publisher/achs/journals/content/oprdfk/0/oprdfk.ahead-of-print/acs.oprd.8b00406/20190123/images/medium/op-2018-00406p_0008.gif" src="https://pubs.acs.org/appl/literatum/publisher/achs/journals/content/oprdfk/0/oprdfk.ahead-of-print/acs.oprd.8b00406/20190123/images/medium/op-2018-00406p_0008.gif" style="height: auto; max-width: 100%;" /></a></div>
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An advanced process for large scale (500 g) preparation of a (3<i>Z</i>,5<i>Z</i>)-2,7-dihydro-1<i>H</i>-azepine-derived chiral tridentate ligand (Hamari ligand), widely used for asymmetric synthesis of tailor-made α-amino acids via the corresponding glycine Schiff base Ni(II) complex, is disclosed. The process includes amidation, bis-alkylation, and precipitation/purification of the target compound by TFA as a counterion.</div>
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<span class="hlFld-Title">Large Scale Synthesis of Chiral (3<i>Z</i>,5<i>Z</i>)-2,7-Dihydro-1<i>H</i>-azepine-Derived Hamari Ligand for General Asymmetric Synthesis of Tailor-Made Amino Acids</span></div>
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<span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="https://pubs.acs.org/author/Takahashi%2C+Motohiro" href="https://pubs.acs.org/author/Takahashi%2C+Motohiro" id="authors">Motohiro Takahashi</a></span><a class="ref" data-mce-href="https://pubs.acs.org/doi/10.1021/acs.oprd.8b00406#cor1" href="https://pubs.acs.org/doi/10.1021/acs.oprd.8b00406#cor1">*</a><span class="NLM_xref-aff"><sup>†</sup></span><span class="orcid-link-icon"> <a data-mce-href="http://orcid.org/0000-0001-5089-2033" href="http://orcid.org/0000-0001-5089-2033" target="_blank"><img alt="" data-mce-src="https://pubs.acs.org/templates/jsp/images/orcid.png" src="https://pubs.acs.org/templates/jsp/images/orcid.png" style="height: auto; max-width: 100%;" /></a></span></span><span class="NLM_x">, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="https://pubs.acs.org/author/Moriwaki%2C+Hiroki" href="https://pubs.acs.org/author/Moriwaki%2C+Hiroki" id="authors">Hiroki Moriwaki</a></span><span class="NLM_xref-aff"><sup>†</sup></span></span><span class="NLM_x">, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="https://pubs.acs.org/author/Miwa%2C+Toshio" href="https://pubs.acs.org/author/Miwa%2C+Toshio" id="authors">Toshio Miwa</a></span><span class="NLM_xref-aff"><sup>†</sup></span></span><span class="NLM_x">, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="https://pubs.acs.org/author/Hoang%2C+Brittanie" href="https://pubs.acs.org/author/Hoang%2C+Brittanie" id="authors">Brittanie Hoang</a></span><span class="NLM_xref-aff"><sup>‡</sup></span></span><span class="NLM_x">, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="https://pubs.acs.org/author/Wang%2C+Peng" href="https://pubs.acs.org/author/Wang%2C+Peng" id="authors">Peng Wang</a></span><span class="NLM_xref-aff"><sup>‡</sup></span></span><span class="NLM_x">, and </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="https://pubs.acs.org/author/Soloshonok%2C+Vadim+A" href="https://pubs.acs.org/author/Soloshonok%2C+Vadim+A" id="authors">Vadim A. Soloshonok</a></span><a class="ref" data-mce-href="https://pubs.acs.org/doi/10.1021/acs.oprd.8b00406#cor2" href="https://pubs.acs.org/doi/10.1021/acs.oprd.8b00406#cor2">*</a><span class="NLM_xref-aff"><sup>§</sup></span><span class="NLM_xref-aff"><sup>∥</sup></span><span class="orcid-link-icon"> <a data-mce-href="http://orcid.org/0000-0003-0681-4526" href="http://orcid.org/0000-0003-0681-4526" target="_blank"><img alt="" data-mce-src="https://pubs.acs.org/templates/jsp/images/orcid.png" src="https://pubs.acs.org/templates/jsp/images/orcid.png" style="height: auto; max-width: 100%;" /></a></span></span></div>
<div class="affiliations">
<div id="aff1">
<sup>†</sup> <span class="institution">Hamari Chemicals Ltd</span>., <span class="addr-line">1-4-29 Kunijima, Higashi-Yodogawa-ku</span>, Osaka 533-0024, <span class="country">Japan</span></div>
<div id="aff2">
<sup>‡</sup> <span class="institution">Hamari Chemicals USA, San Diego Research Center</span>, <span class="addr-line">11494 Sorrento Valley Road</span>, San Diego, California 92121, <span class="country">United States</span></div>
<div id="aff3">
<sup>§</sup> <span class="institution">Department of Organic Chemistry I, Faculty of Chemistry</span>, <span class="institution">University of the Basque Country UPV/EHU</span>, <span class="addr-line">Paseo Manuel Lardizábal 3</span>, 20018 San Sebastián, <span class="country">Spain</span></div>
<div id="aff4">
<sup>∥</sup> <span class="institution">IKERBASQUE, Basque Foundation for Science</span>, <span class="addr-line">María Díaz de Haro 3, Plaza Bizkaia</span>, 48013 Bilbao, <span class="country">Spain</span></div>
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<div class="generic-sec">
<div id="citation">
<cite>Org. Process Res. Dev.</cite>, Article ASAP</div>
<div id="doi">
<strong>DOI: </strong>10.1021/acs.oprd.8b00406</div>
<div id="pubDate">
Publication Date (Web): January 18, 2019</div>
<div id="artCopyright">
Copyright © 2019 American Chemical Society</div>
<div id="correspondence">
*E-mail: <a data-mce-href="mailto:motohiro-takahashi@hamari.co.jp" href="mailto:motohiro-takahashi@hamari.co.jp">motohiro-takahashi@hamari.co.jp</a>., *E-mail: <a data-mce-href="mailto:vadym.soloshonok@ehu.es" href="mailto:vadym.soloshonok@ehu.es">vadym.soloshonok@ehu.es</a>.</div>
<div id="specialIssueNotice">
This article is part of the <a data-mce-href="https://pubs.acs.org/toc/oprdfk" href="https://pubs.acs.org/toc/oprdfk">Japanese Society for Process Chemistry</a> special issue.</div>
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<a data-mce-href="https://pubs.acs.org/doi/suppl/10.1021/acs.oprd.8b00406/suppl_file/op8b00406_si_001.pdf" href="https://pubs.acs.org/doi/suppl/10.1021/acs.oprd.8b00406/suppl_file/op8b00406_si_001.pdf">/////////</a>/////////</div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-43130751777072834622018-10-14T09:22:00.000+05:302018-10-21T12:26:01.650+05:30Kalyan Kumar Pasunooti, 5-Methylisoxazole-3-carboxamide-Directed Palladium-Catalyzed γ-C(sp3)–H Acetoxylation and Application to the Synthesis of γ-Mercapto Amino Acids for Native Chemical Ligation<div dir="ltr" style="text-align: left;" trbidi="on">
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<img alt="Abstract Image" data-mce-src="https://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2016/orlef7.2016.18.issue-11/acs.orglett.6b01160/20160527/images/medium/ol-2016-01160a_0008.gif" src="https://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2016/orlef7.2016.18.issue-11/acs.orglett.6b01160/20160527/images/medium/ol-2016-01160a_0008.gif" style="height: auto; max-width: 100%;" /></div>
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Palladium-catalyzed acetoxylation of the primary γ-C(sp<sup>3</sup>)–H bonds in the amino acids Val, Thr, and Ile was achieved using a newly discovered 5-methylisoxazole-3-carboxamide directing group. The γ-acetoxylated α-amino acid derivatives could be easily converted to γ-mercapto amino acids, which are useful for native chemical ligation (NCL). The first application of NCL at isoleucine in the semisynthesis of a <i>Xenopus</i> histone H3 protein was also demonstrated.</div>
<h1 class="articleTitle" style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif;">
<span class="hlFld-Title">5-Methylisoxazole-3-carboxamide-Directed Palladium-Catalyzed γ-C(sp<sup>3</sup>)–H Acetoxylation and Application to the Synthesis of γ-Mercapto Amino Acids for Native Chemical Ligation</span></h1>
<div id="articleMeta" style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
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<span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="https://pubs.acs.org/author/Pasunooti%2C+Kalyan+Kumar" href="https://pubs.acs.org/author/Pasunooti%2C+Kalyan+Kumar" id="authors">Kalyan Kumar Pasunooti</a></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="https://pubs.acs.org/author/Yang%2C+Renliang" href="https://pubs.acs.org/author/Yang%2C+Renliang" id="authors">Renliang Yang</a></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="https://pubs.acs.org/author/Banerjee%2C+Biplab" href="https://pubs.acs.org/author/Banerjee%2C+Biplab" id="authors">Biplab Banerjee</a></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="https://pubs.acs.org/author/Yap%2C+Terence" href="https://pubs.acs.org/author/Yap%2C+Terence" id="authors">Terence Yap</a></span>, and </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="https://pubs.acs.org/author/Liu%2C+Chuan-Fa" href="https://pubs.acs.org/author/Liu%2C+Chuan-Fa" id="authors">Chuan-Fa Liu</a></span><a class="ref" data-mce-href="https://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b01160#cor1" href="https://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b01160#cor1"><sup>*</sup></a></span></div>
<div class="affiliations">
<div id="aff1">
School of Biological Sciences, <span class="institution">Nanyang Technological University</span>, <span class="country">Singapore</span> 637551</div>
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<div class="wrapper">
<div class="generic-sec">
<div id="citation">
<cite>Org. Lett.</cite>, <span class="citation_year">2016</span>, <span class="citation_volume">18</span> (11), pp 2696–2699</div>
<div id="doi">
<strong>DOI: </strong>10.1021/acs.orglett.6b01160</div>
<div id="pubDate">
Publication Date (Web): May 24, 2016</div>
<div id="artCopyright">
Copyright © 2016 American Chemical Society</div>
<div id="correspondence">
*E-mail: <a data-mce-href="mailto:cfliu@ntu.edu.sg" href="mailto:cfliu@ntu.edu.sg">cfliu@ntu.edu.sg</a>.</div>
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<a data-mce-href="https://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b01160" href="https://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b01160">https://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b01160</a></div>
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<img alt="Dr. Kalyan Kumar Pasunooti" data-mce-src="https://media.licdn.com/dms/image/C5603AQFgO3HiHNMZYw/profile-displayphoto-shrink_800_800/0?e=1544659200&v=beta&t=IH3X8BjCh7k2Wkp30vJgmoQmfgcOpVnhI_mP4UyFfFw" src="https://media.licdn.com/dms/image/C5603AQFgO3HiHNMZYw/profile-displayphoto-shrink_800_800/0?e=1544659200&v=beta&t=IH3X8BjCh7k2Wkp30vJgmoQmfgcOpVnhI_mP4UyFfFw" style="height: auto; max-width: 100%;" /></div>
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<div id="authors" style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
<span class="hlFld-ContribAuthor"><a data-mce-href="https://pubs.acs.org/author/Pasunooti%2C+Kalyan+Kumar" href="https://pubs.acs.org/author/Pasunooti%2C+Kalyan+Kumar" id="authors">Kalyan Kumar Pasunooti</a>,</span><br />
<span class="hlFld-ContribAuthor"><br /></span>
<div class="MsoNormalCxSpFirst" style="margin-bottom: 6.0pt; mso-add-space: auto; text-align: justify;">
<span lang="EN-SG">Dr. Kalyan Kumar Pasunooti pursued his PhD
degree from Nanyang Technological University (NTU) (</span><span lang="EN-SG"><a href="http://www.ntu.edu.sg/">www.ntu.edu.sg</a></span><span lang="EN-SG">),
Singapore (2007 – 2011) in the field of Medicinal, Peptide & Protein
chemistry. His graduate research work is focused on “<i>Synthesis of bioactive amino acid building blocks and their
applications towards the peptides and glycopeptides</i>.” His have total 16
years of academic and industry experience with major multinationals companies
& academic institutions and have worked with many collaborative professors
around the globe. He authored with more than 28 international peer-reviewed
high impact publications such as PNAS, Wily (<i>Angew Chemie</i>), RSC (<i>Chem Comm</i>
and <i>Org Biomol Chem</i>), most of
American Chemical Society journals (<i>Journal
of American Chemical Society</i>, <i>Org.
Lett.</i>, <i>ACS Chem Bio</i>, <i>J Comb Chem</i> and <i>Bioconugate Chem</i>) and Elsevier (Tetrahedron Letters) journals which
are featured many times in Chem. Eng. News and other journals. He holds American
patent while work with Johns Hopkins-School of Medicine, USA and this molecule
in phase II clinical trials for treating cancer.<o:p></o:p></span></div>
<div class="MsoNormalCxSpMiddle" style="margin-bottom: 6.0pt; mso-add-space: auto; text-align: justify;">
<span lang="EN-SG">Prior to his graduate studies, he spent 5
years as a research scientist in reputable research organizations namely GVK
Bio, India (</span><span lang="EN-SG"><a href="http://www.gvkbio.com/">www.gvkbio.com</a></span><span lang="EN-SG">)
(2006-2007) and Dr. Reddy’s Laboratories Ltd (</span><span lang="EN-SG"><a href="http://www.drreddys.com/">www.drreddys.com</a></span><span lang="EN-SG">)
(2003-2006) in India. After his PhD graduation, he worked for world leading research
institutes such as Johns Hopkins-School of Medicine, USA (</span><span lang="EN-SG"><a href="http://www.hopkinsmedicne.org/">www.hopkinsmedicne.org</a></span><span lang="EN-SG">)
(2012-2013), Nanyang Technological University-NTU, Singapore) (</span><span lang="EN-SG"><a href="http://www.ntu.edu.sg/">www.ntu.edu.sg</a></span><span lang="EN-SG">)
(2013 – 2017) and Singapore MIT Alliance for research & Technology-SMART (</span><span lang="EN-SG"><a href="http://www.smart.mit.edu/">www.smart.mit.edu</a></span><span lang="EN-SG">)
(2017–2018). His research interests focused on development of next generation
biologically relevant peptide & protein therapeutics using their newly
discovered methodologies for biomedical applications. <o:p></o:p></span></div>
<div class="MsoNormalCxSpMiddle" style="margin-bottom: 6.0pt; mso-add-space: auto; text-align: justify;">
<span lang="EN-SG">He has excellent skills in designing
synthesis, purification and characterization of complex peptide and small
molecules for medicinal chemistry applications. He gained extensive experience
in Medicinal, Carbohydrate, Peptide & Protein and nucleotide &
nucleoside Chemistry and familiar with modern methods and experienced in
designing & executing synthesis for various bioactive peptide and small
molecule inhibitors. He well versed in synthesis and characterization of
complex organic molecules and with the analytical data interpretation. <o:p></o:p></span></div>
<span class="hlFld-ContribAuthor">
</span><br />
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<div>
<h1 class="pv-top-card-section__name inline t-24 t-black t-normal">
Dr. Kalyan Kumar Pasunooti</h1>
Research Scientist at Singapore-MIT Alliance for Research & Technology Centre</div>
<h3 class="pv-top-card-section__location t-16 t-black--light t-normal mt1 inline-block">
Singapore'</h3>
<div class="ember-view" id="ember3708">
<br />
<section class="pv-profile-section pv-top-card-section artdeco-container-card ember-view" id="ember3713"><div class="pv-top-card-section__summary pv-top-card-section__summary--with-content mt4 ember-view" id="ember3788">
<div class="pv-top-card-section__summary-text mt4 ember-view" id="ember3792">
<span class="lt-line-clamp__line">Accomplished Peptide, Protein and Medicinal chemist with 16 years of academic and industrial</span><span class="lt-line-clamp__line">experience in the field of drug discovery and development. Specializations: Peptide & Protein Chemistry,</span><span class="lt-line-clamp__line lt-line-clamp__line--last">Medicinal Chemistry (Drug Discovery and Development) and Chemical Biology.</span></div>
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<section class="pv-profile-section experience-section ember-view" id="experience-section"><header class="pv-profile-section__card-header"><h2 class="pv-profile-section__card-heading t-20 t-black t-normal">
Experience<img alt="Singapore-MIT Alliance for Research & Technology Centre" class="lazy-image pv-entity__logo-img pv-entity__logo-img EntityPhoto-square-5 loaded" data-mce-src="https://media.licdn.com/dms/image/C560BAQEFRQob0B8sdw/company-logo_400_400/0?e=1547683200&v=beta&t=HuGbQy-9g4S0BlGxLl9DzriGyuoUW42Qkpp12qD_DHc" height="200" src="https://media.licdn.com/dms/image/C560BAQEFRQob0B8sdw/company-logo_400_400/0?e=1547683200&v=beta&t=HuGbQy-9g4S0BlGxLl9DzriGyuoUW42Qkpp12qD_DHc" style="height: auto; max-width: 100%;" width="200" /></h2>
<h2 class="pv-profile-section__card-heading t-20 t-black t-normal">
Research Scientist</h2>
</header>
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<h4 class="t-16 t-black t-normal">
<span class="visually-hidden">Company Name</span><span class="pv-entity__secondary-title">Singapore-MIT Alliance for Research & Technology Centre</span></h4>
<div class="display-flex">
<h4 class="pv-entity__date-range t-14 t-black--light t-normal">
<span class="visually-hidden">Dates Employed</span>Jul 2017 – Present</h4>
<h4 class="t-14 t-black--light t-normal">
<span class="visually-hidden">Employment Duration</span><span class="pv-entity__bullet-item-v2">1 yr 4 mos</span></h4>
</div>
<h4 class="pv-entity__location t-14 t-black--light t-normal block">
<span class="visually-hidden">Location</span>Singapore</h4>
</div>
<div class="pv-entity__extra-details ember-view" id="ember4344">
<div class="pv-entity__description t-14 t-black t-normal ember-view" id="ember4346">
<span class="lt-line-clamp__line lt-line-clamp__line--last">Medicinal Chemistry and Drug Discovery</span></div>
</div>
</li>
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<img alt="Nanyang Technological University, Singapore" class="lazy-image pv-entity__logo-img pv-entity__logo-img EntityPhoto-square-5 loaded" data-mce-src="https://media.licdn.com/dms/image/C4D0BAQG0nfM0ZH4emA/company-logo_400_400/0?e=1547683200&v=beta&t=F12kGvcwgmiwWCAcCfB3Lf0GPq6SmAXTO5pZ-2eBK3E" height="200" src="https://media.licdn.com/dms/image/C4D0BAQG0nfM0ZH4emA/company-logo_400_400/0?e=1547683200&v=beta&t=F12kGvcwgmiwWCAcCfB3Lf0GPq6SmAXTO5pZ-2eBK3E" style="height: auto; max-width: 100%;" width="200" /></div>
<div class="pv-entity__summary-info pv-entity__summary-info--background-section mb2">
<h3 class="t-16 t-black t-bold">
Research Fellow</h3>
<h4 class="t-16 t-black t-normal">
<span class="visually-hidden">Company Name</span><span class="pv-entity__secondary-title">Nanyang Technological University, Singapore</span></h4>
<div class="display-flex">
<h4 class="pv-entity__date-range t-14 t-black--light t-normal">
<span class="visually-hidden">Dates Employed</span>Oct 2013 – Jun 2017</h4>
<h4 class="t-14 t-black--light t-normal">
<span class="visually-hidden">Employment Duration</span><span class="pv-entity__bullet-item-v2">3 yrs 9 mos</span></h4>
</div>
<h4 class="pv-entity__location t-14 t-black--light t-normal block">
<span class="visually-hidden">Location</span>Singapore</h4>
</div>
<div class="pv-entity__extra-details ember-view" id="ember4353">
<div class="pv-entity__description t-14 t-black t-normal ember-view" id="ember4355">
<span class="lt-line-clamp__line lt-line-clamp__line--last">Peptide & Protein Chemistry and Medicinal Chemistry</span></div>
</div>
</li>
<li class="pv-profile-section__card-item-v2 pv-profile-section pv-position-entity ember-view" id="281126443"><div class="pv-entity__logo company-logo">
<img alt="Johns Hopkins Medicine" class="lazy-image pv-entity__logo-img pv-entity__logo-img EntityPhoto-square-5 loaded" data-mce-src="https://media.licdn.com/dms/image/C560BAQHPOfV7Wl0x-A/company-logo_400_400/0?e=1547683200&v=beta&t=rEq-pzMSEi4OgQJkNoF1Qy--5gz7SCp1nUBAiXaWUr8" height="200" src="https://media.licdn.com/dms/image/C560BAQHPOfV7Wl0x-A/company-logo_400_400/0?e=1547683200&v=beta&t=rEq-pzMSEi4OgQJkNoF1Qy--5gz7SCp1nUBAiXaWUr8" style="height: auto; max-width: 100%;" width="200" /></div>
<div class="pv-entity__summary-info pv-entity__summary-info--background-section mb2">
<h3 class="t-16 t-black t-bold">
Postdoctoral Fellow</h3>
<h4 class="t-16 t-black t-normal">
<span class="visually-hidden">Company Name</span><span class="pv-entity__secondary-title">Johns Hopkins Medicine</span></h4>
<div class="display-flex">
<h4 class="pv-entity__date-range t-14 t-black--light t-normal">
<span class="visually-hidden">Dates Employed</span>May 2012 – Sep 2013</h4>
<h4 class="t-14 t-black--light t-normal">
<span class="visually-hidden">Employment Duration</span><span class="pv-entity__bullet-item-v2">1 yr 5 mos</span></h4>
</div>
<h4 class="pv-entity__location t-14 t-black--light t-normal block">
<span class="visually-hidden">Location</span>Baltimore, Maryland Area</h4>
</div>
<div class="pv-entity__extra-details ember-view" id="ember4362">
<div class="pv-entity__description t-14 t-black t-normal ember-view" id="ember4364">
<span class="lt-line-clamp__line lt-line-clamp__line--last">Medicinal chemistry, Drug Discovery, Pharmacology and Chemical Biology</span></div>
</div>
</li>
<li class="pv-profile-section__card-item-v2 pv-profile-section pv-position-entity ember-view" id="228457123"><div class="pv-entity__logo company-logo">
<img alt="Nanyang Technological University" class="lazy-image pv-entity__logo-img pv-entity__logo-img EntityPhoto-square-5 loaded" data-mce-src="https://media.licdn.com/dms/image/C4D0BAQG0nfM0ZH4emA/company-logo_400_400/0?e=1547683200&v=beta&t=F12kGvcwgmiwWCAcCfB3Lf0GPq6SmAXTO5pZ-2eBK3E" height="200" src="https://media.licdn.com/dms/image/C4D0BAQG0nfM0ZH4emA/company-logo_400_400/0?e=1547683200&v=beta&t=F12kGvcwgmiwWCAcCfB3Lf0GPq6SmAXTO5pZ-2eBK3E" style="height: auto; max-width: 100%;" width="200" /></div>
<div class="pv-entity__summary-info pv-entity__summary-info--background-section mb2">
<h3 class="t-16 t-black t-bold">
Postdoctoral Associate</h3>
<h4 class="t-16 t-black t-normal">
<span class="visually-hidden">Company Name</span><span class="pv-entity__secondary-title">Nanyang Technological University</span></h4>
<div class="display-flex">
<h4 class="pv-entity__date-range t-14 t-black--light t-normal">
<span class="visually-hidden">Dates Employed</span>Jul 2011 – Mar 2012</h4>
<h4 class="t-14 t-black--light t-normal">
<span class="visually-hidden">Employment Duration</span><span class="pv-entity__bullet-item-v2">9 mos</span></h4>
</div>
<h4 class="pv-entity__location t-14 t-black--light t-normal block">
<span class="visually-hidden">Location</span>Singapore</h4>
</div>
<div class="pv-entity__extra-details ember-view" id="ember4371">
<div class="pv-entity__description t-14 t-black t-normal ember-view" id="ember4373">
<span class="lt-line-clamp__line lt-line-clamp__line--last">Organic synthesis, Peptide & Carbohydrate chemistry and Medicinal chemistry.</span></div>
</div>
</li>
<li class="pv-profile-section__card-item-v2 pv-profile-section pv-position-entity ember-view" id="228200063"><div class="pv-entity__logo company-logo">
<img alt="GVK Biosciences" class="lazy-image pv-entity__logo-img pv-entity__logo-img EntityPhoto-square-5 loaded" data-mce-src="https://media.licdn.com/dms/image/C510BAQHCsxmViVaBOg/company-logo_400_400/0?e=1547683200&v=beta&t=dzyxnDRl-g78K3Q4CAso-t5Yk40H-n3Za84LKOgOPSo" height="200" src="https://media.licdn.com/dms/image/C510BAQHCsxmViVaBOg/company-logo_400_400/0?e=1547683200&v=beta&t=dzyxnDRl-g78K3Q4CAso-t5Yk40H-n3Za84LKOgOPSo" style="height: auto; max-width: 100%;" width="200" /></div>
<div class="pv-entity__summary-info pv-entity__summary-info--background-section mb2">
<h3 class="t-16 t-black t-bold">
Senior Research Associate in Medicinal Chemistry</h3>
<h4 class="t-16 t-black t-normal">
<span class="visually-hidden">Company Name</span><span class="pv-entity__secondary-title">GVK Biosciences</span></h4>
<div class="display-flex">
<h4 class="pv-entity__date-range t-14 t-black--light t-normal">
<span class="visually-hidden">Dates Employed</span>Jan 2007 – Jul 2007</h4>
<h4 class="t-14 t-black--light t-normal">
<span class="visually-hidden">Employment Duration</span><span class="pv-entity__bullet-item-v2">7 mos</span></h4>
</div>
<h4 class="pv-entity__location t-14 t-black--light t-normal block">
<span class="visually-hidden">Location</span>Hyderabad Area, India</h4>
</div>
<div class="pv-entity__extra-details ember-view" id="ember4380">
<div class="pv-entity__description t-14 t-black t-normal ember-view" id="ember4382">
<span class="lt-line-clamp__line lt-line-clamp__line--last">Synthesis of bioactive molecules for medicinal chemistry applications.</span></div>
</div>
</li>
<li class="pv-profile-section__card-item-v2 pv-profile-section pv-position-entity ember-view" id="228200230"><div class="pv-entity__logo company-logo">
<img alt="Dr. Reddy's Laboratories" class="lazy-image pv-entity__logo-img pv-entity__logo-img EntityPhoto-square-5 loaded" data-mce-src="https://media.licdn.com/dms/image/C560BAQEWdli6is_B1A/company-logo_400_400/0?e=1547683200&v=beta&t=iIQj5dObIAQRK-hB-nlGeuw7VArdngQd6xZ1u0ktZ9U" height="200" src="https://media.licdn.com/dms/image/C560BAQEWdli6is_B1A/company-logo_400_400/0?e=1547683200&v=beta&t=iIQj5dObIAQRK-hB-nlGeuw7VArdngQd6xZ1u0ktZ9U" style="height: auto; max-width: 100%;" width="200" /></div>
<div class="pv-entity__summary-info pv-entity__summary-info--background-section mb2">
<h3 class="t-16 t-black t-bold">
Junior Scientist in Medicinal Chemistry (Anti-Infective group)</h3>
<h4 class="t-16 t-black t-normal">
<span class="visually-hidden">Company Name</span><span class="pv-entity__secondary-title">Dr. Reddy's Laboratories</span></h4>
<div class="display-flex">
<h4 class="pv-entity__date-range t-14 t-black--light t-normal">
<span class="visually-hidden">Dates Employed</span>Aug 2003 – Dec 2006</h4>
<h4 class="t-14 t-black--light t-normal">
<span class="visually-hidden">Employment Duration</span><span class="pv-entity__bullet-item-v2">3 yrs 5 mos</span></h4>
</div>
<h4 class="pv-entity__location t-14 t-black--light t-normal block">
<span class="visually-hidden">Location</span>Hyderabad Area, India</h4>
</div>
<div class="pv-entity__extra-details ember-view" id="ember4389">
<div class="pv-entity__description t-14 t-black t-normal ember-view" id="ember4391">
<span class="lt-line-clamp__line">Medicinal chemistry (Anti-Infective group): My work entails design and synthesis of new</span><span class="lt-line-clamp__line">oxazolidinone derivatives and new chemical entities as novel antibacterial agents. As a research</span><span class="lt-line-clamp__line">scientist my job demanded me to carry out extensive literature survey to design possible synthetic</span><span class="lt-line-clamp__line lt-line-clamp__line--last">routes for a proposed molecule and to carry out the total synthetic part in the laborator<span class="lt-line-clamp__ellipsis">... <a class="lt-line-clamp__more" data-mce-href="https://www.linkedin.com/in/dr-kalyan-kumar-pasunooti-13b10633/#" href="https://www.linkedin.com/in/dr-kalyan-kumar-pasunooti-13b10633/#">See more</a></span></span></div>
</div>
</li>
<div class="pv-experience-section__see-more pv-profile-section__actions-inline ember-view" id="ember4183">
Education</div>
</section></div>
<div class="pv-profile-section-pager ember-view" id="ember4184">
<br />
<section class="pv-profile-section education-section ember-view" id="education-section"><header class="pv-profile-section__card-header"></header><ul class="pv-profile-section__section-info section-info pv-profile-section__section-info--has-no-more ember-view" id="ember4194">
<li class="pv-profile-section__sortable-item pv-profile-section__section-info-item relative pv-profile-section__sortable-item--v2 sortable-item ember-view" id="ember4202"><div class="pv-profile-section__sortable-card-item pv-education-entity pv-profile-section__card-item ember-view" id="86957023">
<div class="pv-entity__logo">
<img alt="Nanyang Technological University" class="lazy-image pv-entity__logo-img pv-entity__logo-img EntityPhoto-square-4 loaded" data-mce-src="https://media.licdn.com/dms/image/C4D0BAQG0nfM0ZH4emA/company-logo_400_400/0?e=1547683200&v=beta&t=F12kGvcwgmiwWCAcCfB3Lf0GPq6SmAXTO5pZ-2eBK3E" height="200" src="https://media.licdn.com/dms/image/C4D0BAQG0nfM0ZH4emA/company-logo_400_400/0?e=1547683200&v=beta&t=F12kGvcwgmiwWCAcCfB3Lf0GPq6SmAXTO5pZ-2eBK3E" style="height: auto; max-width: 100%;" width="200" /></div>
<div class="pv-entity__summary-info pv-entity__summary-info--background-section">
<div class="pv-entity__degree-info">
<h3 class="pv-entity__school-name t-16 t-black t-bold">
Nanyang Technological University</h3>
<div class="pv-entity__secondary-title pv-entity__degree-name pv-entity__secondary-title t-14 t-black t-normal">
<span class="visually-hidden">Degree Name</span><span class="pv-entity__comma-item">PhD</span></div>
<div class="pv-entity__secondary-title pv-entity__fos pv-entity__secondary-title t-14 t-black--light t-normal">
<span class="visually-hidden">Field Of Study</span><span class="pv-entity__comma-item">Organic and Bioorganic chemistry</span></div>
</div>
<div class="pv-entity__dates t-14 t-black--light t-normal">
<span class="visually-hidden">Dates attended or expected graduation</span><time>2007</time> – <time>2011</time></div>
</div>
</div>
</li>
<li class="pv-profile-section__sortable-item pv-profile-section__section-info-item relative pv-profile-section__sortable-item--v2 sortable-item ember-view" id="ember4215"><div class="pv-profile-section__sortable-card-item pv-education-entity pv-profile-section__card-item ember-view" id="86956532">
<div class="pv-entity__logo">
<img alt="Osmania University" class="lazy-image pv-entity__logo-img pv-entity__logo-img EntityPhoto-square-4 loaded" data-mce-src="https://media.licdn.com/dms/image/C4E0BAQGWO2PFCtwq6Q/company-logo_400_400/0?e=1547683200&v=beta&t=eakW0Ws9qtuIZob1IPk1_YEkRtVXye-V2wPL9WNKAgk" height="200" src="https://media.licdn.com/dms/image/C4E0BAQGWO2PFCtwq6Q/company-logo_400_400/0?e=1547683200&v=beta&t=eakW0Ws9qtuIZob1IPk1_YEkRtVXye-V2wPL9WNKAgk" style="height: auto; max-width: 100%;" width="200" /></div>
<div class="pv-entity__summary-info pv-entity__summary-info--background-section">
<div class="pv-entity__degree-info">
<h3 class="pv-entity__school-name t-16 t-black t-bold">
Osmania University</h3>
<div class="pv-entity__secondary-title pv-entity__degree-name pv-entity__secondary-title t-14 t-black t-normal">
<span class="visually-hidden">Degree Name</span><span class="pv-entity__comma-item">M. Sc</span></div>
<div class="pv-entity__secondary-title pv-entity__fos pv-entity__secondary-title t-14 t-black--light t-normal">
<span class="visually-hidden">Field Of Study</span><span class="pv-entity__comma-item">Physical Organic Chemistry</span></div>
</div>
<div class="pv-entity__dates t-14 t-black--light t-normal">
<span class="visually-hidden">Dates attended or expected graduation</span><time>2000</time> – <time>2002</time></div>
</div>
</div>
</li>
<li class="pv-profile-section__sortable-item pv-profile-section__section-info-item relative pv-profile-section__sortable-item--v2 sortable-item ember-view" id="ember4220"><div class="pv-profile-section__sortable-card-item pv-education-entity pv-profile-section__card-item ember-view" id="86956937">
<div class="pv-entity__logo">
<img alt="Kakatiya University" class="lazy-image pv-entity__logo-img pv-entity__logo-img EntityPhoto-square-4 ghost-school loaded" src="data:image/gif;base64,R0lGODlhAQABAIAAAAAAAP///yH5BAEAAAAALAAAAAABAAEAAAIBRAA7" style="height: auto; max-width: 100%;" /></div>
<div class="pv-entity__summary-info pv-entity__summary-info--background-section">
<div class="pv-entity__degree-info">
<h3 class="pv-entity__school-name t-16 t-black t-bold">
Kakatiya University</h3>
<div class="pv-entity__secondary-title pv-entity__degree-name pv-entity__secondary-title t-14 t-black t-normal">
<span class="visually-hidden">Degree Name</span><span class="pv-entity__comma-item">B. Sc,</span></div>
<div class="pv-entity__secondary-title pv-entity__fos pv-entity__secondary-title t-14 t-black--light t-normal">
<span class="visually-hidden">Field Of Study</span><span class="pv-entity__comma-item">Mathematics Physics Chemistry</span></div>
</div>
<div class="pv-entity__dates t-14 t-black--light t-normal">
<span class="visually-hidden">Dates attended or expected graduation</span><time>1996</time> – <time>1999</time></div>
</div>
</div>
</li>
</ul>
</section></div>
</section></div>
<div class="pv-deferred-area ember-view" id="ember3802">
</div>
</div>
</div>
</section></div>
<div class="profile-detail">
</div>
<div class="pv-top-card-v2-section__actions mt2 display-flex">
Research Scientist at <a class="profileLink" data-hovercard-prefer-more-content-show="1" data-hovercard="/ajax/hovercard/page.php?id=130773473660988&extragetparams=%7B%22eid%22%3A%22ARAzR3I1Y1JqA9Cugp4JQPyTYzlhcGskr9om7QEfLCYik9mAJVXNRLiBrinpv9-NQL-1r5xtNJKIskmH%22%2C%22timeline_context_item_type%22%3A%22intro_card_work%22%2C%22timeline_context_item_source%22%3A100008126776933%2C%22fref%22%3A%22tag%22%7D" data-mce-href="https://www.facebook.com/smart.mit/?eid=ARAzR3I1Y1JqA9Cugp4JQPyTYzlhcGskr9om7QEfLCYik9mAJVXNRLiBrinpv9-NQL-1r5xtNJKIskmH&timeline_context_item_type=intro_card_work&timeline_context_item_source=100008126776933&fref=tag" href="https://www.facebook.com/smart.mit/?eid=ARAzR3I1Y1JqA9Cugp4JQPyTYzlhcGskr9om7QEfLCYik9mAJVXNRLiBrinpv9-NQL-1r5xtNJKIskmH&timeline_context_item_type=intro_card_work&timeline_context_item_source=100008126776933&fref=tag">Singapore-MIT Alliance for Research and Technology</a></div>
</div>
<div class="affiliations" style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
<ul class="uiList _3-8x _2pic _4kg" id="u_ps_fetchstream_12_1_1">
<li class="_1zw6 _md0 _5h-n _5vb9" data-profile-intro-card="1" data-store="{"event":"context_item_view_click"}"><div class="clearfix">
<br />
<div class="_42ef">
<div class="textContent">
<div class="_50f3">
Research Fellow at <a class="profileLink" data-hovercard-prefer-more-content-show="1" data-hovercard="/ajax/hovercard/page.php?id=188991601140026&extragetparams=%7B%22eid%22%3A%22ARCpFfSjcd_DFXDywlwpSDMTQN5z5vzYX1ycd-vc6mjBFbY76nSrC16Hx96pJaErscnXNhdTQs1DpUJT%22%2C%22timeline_context_item_type%22%3A%22intro_card_work%22%2C%22timeline_context_item_source%22%3A100008126776933%2C%22fref%22%3A%22tag%22%7D" data-mce-href="https://www.facebook.com/NTUsg/?eid=ARCpFfSjcd_DFXDywlwpSDMTQN5z5vzYX1ycd-vc6mjBFbY76nSrC16Hx96pJaErscnXNhdTQs1DpUJT&timeline_context_item_type=intro_card_work&timeline_context_item_source=100008126776933&fref=tag" href="https://www.facebook.com/NTUsg/?eid=ARCpFfSjcd_DFXDywlwpSDMTQN5z5vzYX1ycd-vc6mjBFbY76nSrC16Hx96pJaErscnXNhdTQs1DpUJT&timeline_context_item_type=intro_card_work&timeline_context_item_source=100008126776933&fref=tag">Nanyang Technological University, Singapore</a></div>
</div>
</div>
</div>
</li>
<li class="_1zw6 _md0 _5h-n _5vb9" data-profile-intro-card="1" data-store="{"event":"context_item_view_click"}"><div class="clearfix">
<br />
<div class="_42ef">
<div class="textContent">
<div class="_50f3">
Former Post-Doctoral Fellow at <a class="profileLink" data-hovercard-prefer-more-content-show="1" data-hovercard="/ajax/hovercard/page.php?id=108042952549062&extragetparams=%7B%22eid%22%3A%22ARAHw2V4OUO1hVPRiTMiW1HymJbmydniR9PmdB8r5nzHipmh7SnafQ2Flh0l_9rOby7KEAvUIe43cGtr%22%2C%22timeline_context_item_type%22%3A%22intro_card_work%22%2C%22timeline_context_item_source%22%3A100008126776933%2C%22fref%22%3A%22tag%22%7D" data-mce-href="https://www.facebook.com/pages/Johns-Hopkins-School-of-Medicine/108042952549062?eid=ARAHw2V4OUO1hVPRiTMiW1HymJbmydniR9PmdB8r5nzHipmh7SnafQ2Flh0l_9rOby7KEAvUIe43cGtr&timeline_context_item_type=intro_card_work&timeline_context_item_source=100008126776933&fref=tag" href="https://www.facebook.com/pages/Johns-Hopkins-School-of-Medicine/108042952549062?eid=ARAHw2V4OUO1hVPRiTMiW1HymJbmydniR9PmdB8r5nzHipmh7SnafQ2Flh0l_9rOby7KEAvUIe43cGtr&timeline_context_item_type=intro_card_work&timeline_context_item_source=100008126776933&fref=tag">Johns Hopkins School of Medicine</a></div>
</div>
</div>
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</li>
<li class="_1zw6 _md0 _5h-n _5vb9" data-profile-intro-card="1" data-store="{"event":"context_item_view_click"}"><div class="clearfix">
<br />
<div class="_42ef">
<div class="textContent">
<div class="_50f3">
Studied Physical organic chemistry at <a class="profileLink" data-hovercard-prefer-more-content-show="1" data-hovercard="/ajax/hovercard/page.php?id=385427421521001&extragetparams=%7B%22eid%22%3A%22ARAg-0GyT7xxEC2N5tYa9DFmVbltpINjuaVY8rm-_jAsfcrmaKAL1W80Vnt9Pfg36-4ltQElath5gZzl%22%2C%22timeline_context_item_type%22%3A%22intro_card_education%22%2C%22timeline_context_item_source%22%3A100008126776933%2C%22fref%22%3A%22tag%22%7D" data-mce-href="https://www.facebook.com/pages/PG-College-of-Science-SaifabadOsmania-University/385427421521001?eid=ARAg-0GyT7xxEC2N5tYa9DFmVbltpINjuaVY8rm-_jAsfcrmaKAL1W80Vnt9Pfg36-4ltQElath5gZzl&timeline_context_item_type=intro_card_education&timeline_context_item_source=100008126776933&fref=tag" href="https://www.facebook.com/pages/PG-College-of-Science-SaifabadOsmania-University/385427421521001?eid=ARAg-0GyT7xxEC2N5tYa9DFmVbltpINjuaVY8rm-_jAsfcrmaKAL1W80Vnt9Pfg36-4ltQElath5gZzl&timeline_context_item_type=intro_card_education&timeline_context_item_source=100008126776933&fref=tag">PG College of Science, Saifabad/Osmania University</a></div>
</div>
</div>
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<li class="_1zw6 _md0 _5h-n _5vb9" data-profile-intro-card="1" data-store="{"event":"context_item_view_click"}"><div class="clearfix">
<br />
<div class="_42ef">
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-1550380620316844182018-07-18T19:01:00.001+05:302018-07-18T19:01:12.614+05:30National award to Anthony Melvin Crasto for contribution to Pharma society from Times Network for Excellence in HEALTHCARE) | 5th July, 2018 | Taj Lands End, Mumbai, India<div dir="ltr" style="text-align: left;" trbidi="on">
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<h2 style="color: #333333; font-family: georgia, "times new roman", "bitstream charter", times, serif;">
DR ANTHONY MEVIN CRASTO Conferred prestigious individual national award at function for contribution to Pharma society from Times Network, National Awards for Marketing Excellence ( For Excellence in HEALTHCARE) | 5th July, 2018 | Taj Lands End, Mumbai India</h2>
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////////////National award, contribution to Pharma society, Times Network, Excellence in HEALTHCARE, 5th July, 2018, Taj Lands End, Mumbai, India, ANTHONY CRASTO</div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-6122779622549583482018-06-02T09:55:00.001+05:302018-06-02T09:55:16.342+05:30Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles<div dir="ltr" style="text-align: left;" trbidi="on">
<img alt="Graphical abstract: Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles" height="233" src="http://pubs.rsc.org/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=C8GC00987B" width="640" /><br />
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Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles</h2>
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<span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3ADong%20Wang" style="color: #2d7ea9;">Dong Wang</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span> </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3ALinna%20Li" style="color: #2d7ea9;">Linna Li</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span> </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AHairong%20Feng" style="color: #2d7ea9;">Hairong Feng</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span> </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AHua%20Sun" style="color: #2d7ea9;">Hua Sun</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span> </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AFabrice%20Almeida-Veloso" style="color: #2d7ea9;">Fabrice Almeida-Veloso</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">b</span> </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AMarine%20Charavin" style="color: #2d7ea9;">Marine Charavin</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">b</span> </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3APeng%20Yu" style="color: #2d7ea9;">Peng Yu</a><span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span> and </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3ALaurent%20D%C3%A9saubry" style="color: #2d7ea9;">Laurent Désaubry</a><span style="font-size: 16px;">*</span><span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span><span style="position: relative; top: -0.4em; vertical-align: baseline;">b</span><span style="position: relative; top: -0.4em; vertical-align: baseline;">c</span> </span></div>
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<span style="display: table-cell; padding-left: 4px; width: 7px;">*</span><span style="display: table-cell; padding-left: 12px;">Corresponding authors</span></div>
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<span style="display: table-cell; padding-left: 4px; width: 7px;"><span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span></span><span style="display: table-cell; padding-left: 12px;">Sino-French Joint Lab of Food Nutrition/Safety and Medicinal Chemistry, China International Science and Technology Cooperation Base of Food Nutrition/Safety and Medicinal Chemistry, College of Biotechnology, Tianjin University of Science and Technology, Tianjin 300457, China<br /><b>E-mail:</b> <a href="mailto:desaubry@unistra.fr" style="color: #9d3d99;" title="desaubry@unistra.fr">desaubry@unistra.fr</a></span></div>
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<span style="display: table-cell; padding-left: 4px; width: 8px;"><span style="position: relative; top: -0.4em; vertical-align: baseline;">b</span></span><span style="display: table-cell; padding-left: 12px;">Laboratory of Therapeutic Innovation (UMR 7200), University of Strasbourg-CNRS, Faculty of Pharmacy, 67400 Illkirch, France</span></div>
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<span style="display: table-cell; padding-left: 4px; width: 7px;"><span style="position: relative; top: -0.4em; vertical-align: baseline;">c</span></span><span style="display: table-cell; padding-left: 12px;">Laboratory of Biomolecules (UMR7203), Sorbonne University – CNRS, 4 place Jussieu, 75005 Paris, France</span></div>
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Abstract</h3>
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An efficient synthesis of fully substituted 2,3-dihydropyrroles has been achieved in one step through the three-component reaction of amines, aromatic aldehydes and α-ketoamides. This atom-economical and catalyst-free reaction is highly stereoselective and generates underexplored heterocycles in a single step. These compounds were examined in an enzymatic assay that led to the identification of potent α-glucosidase inhibitors, thereby demonstrating the utility of this novel methodology in medicinal chemistry.</div>
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N-(4-Chlorophenyl)-2-oxopropanamide (3a)
Cl
H
N
O
O
3a
Using 4-chloroaniline (1.0 g, 7.8 mmol), in accordance with General Procedure A, the title
compound 3a was obtained (810 mg, 52% yield) as a white solid.
1H NMR (400 MHz,
CDCl3) δ 8.73 (s, 1H), 7.60 (d, J = 8.0 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 2.57 (s, 3H).
13C
NMR (100 MHz, CDCl3) δ 197.1, 157.6, 135.0, 130.6, 129.5, 121.1, 24.2. HRMS (ESI-TOF)
m/z calcd. for C9H7NO2Cl-
[M-H]-
: 196.0171, found 196.0170</div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-20167962502509992702018-03-31T09:01:00.001+05:302018-03-31T09:01:44.207+05:30Catalyst-free and solvent-free hydroboration of aldehydes<div dir="ltr" style="text-align: left;" trbidi="on">
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<i><b>Green Chem.</b></i>, 2018, Advance Article<br /><b>DOI</b>: 10.1039/C8GC00042E, Communication</div>
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Hanna Stachowiak, Joanna Kazmierczak, Krzysztof Kucinski, Grzegorz Hreczycho<br />For the first time, a general method for catalyst-free and solvent-free hydroboration of various aldehydes has been developed</div>
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<a data-mce-href="http://feeds.rsc.org/~r/rss/GC/~3/xtv72-flG7o/C8GC00042E" href="http://feeds.rsc.org/~r/rss/GC/~3/xtv72-flG7o/C8GC00042E">Catalyst-free and solvent-free hydroboration of aldehydes</a></h4>
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Catalyst-free and solvent-free hydroboration of aldehydes</h2>
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<span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AHanna%20Stachowiak" href="http://pubs.rsc.org/en/results?searchtext=Author%3AHanna%20Stachowiak">Hanna Stachowiak</a>,<sup>a</sup> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AJoanna%20Ka%C5%BAmierczak" href="http://pubs.rsc.org/en/results?searchtext=Author%3AJoanna%20Ka%C5%BAmierczak">Joanna Kaźmierczak</a>,<sup>a</sup> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AKrzysztof%20Kuci%C5%84ski" href="http://pubs.rsc.org/en/results?searchtext=Author%3AKrzysztof%20Kuci%C5%84ski">Krzysztof Kuciński</a><sup>a</sup> and </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AGrzegorz%20Hreczycho" href="http://pubs.rsc.org/en/results?searchtext=Author%3AGrzegorz%20Hreczycho">Grzegorz Hreczycho</a>*<sup>a</sup> </span></div>
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*Corresponding authors</div>
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<sup>a</sup>Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, 61-614 Poznań, Poland<br /><b>E-mail:</b> <a data-mce-href="mailto:g.h@amu.edu.pl" href="mailto:g.h@amu.edu.pl" title="g.h@amu.edu.pl">g.h@amu.edu.pl</a></div>
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Abstract</h3>
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A simple catalyst-free and solvent-free method for the hydroboration of various aldehydes bearing a wide array of electron-withdrawing and electron-donating groups was developed. Unlike aldehydes, the addition of boranes to ketones is less efficient and is thus advantageous for the chemoselective reduction of the former ones. It is suggested that the described transformation proceeds with the formation of Lewis acid–base adducts, which facilitates further hydroboration.<br />
4,4,5,5-tetramethyl-2-((4-methylbenzyl)oxy)-1,3,2-dioxaborolane (3b) [1] 4,4,5,5-tetramethyl-2-((4-methylbenzyl)oxy)-1,3,2-dioxaborolane was obtained as colorless oil in 97% yield.<br />
1H NMR (400 MHz, CDCl3) δ (ppm) = 1.29 (s, 12H), 2.36 (s, 3H), 4.91 (s, 2H), 7.17 (d, J = 7.9 Hz, 2H), 7.27-7.30 (m, 2H).<br />
13C NMR (101 MHz, CDCl3) δ (ppm) = 21.3, 24.7, 66.7, 83.0, 127.0, 127.2, 129.1, 129.3, 136.4, 137.1.<br />
11B NMR (128 MHz, CDCl3) δ (ppm) = 22.5.<br />
EA: C14H21BO3 (248.16): calcd.C 67.77; H 8.53; found C 67.66; H 8.47.<br />
<a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR4.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR4.jpg" rel="attachment wp-att-10610"><img alt="STR4" class="alignnone size-full wp-image-10610" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR4.jpg" height="129" src="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR4.jpg" style="height: auto; max-width: 100%;" width="164" /></a> <a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR5.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR5.jpg" rel="attachment wp-att-10611"><img alt="STR5" class="alignnone size-full wp-image-10611" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR5.jpg" height="502" src="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR5.jpg" style="height: auto; max-width: 100%;" width="792" /></a><a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR4-1.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR4-1.jpg" rel="attachment wp-att-10612"><img alt="STR4" class="alignnone size-full wp-image-10612" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR4-1.jpg" height="513" src="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR4-1.jpg" style="height: auto; max-width: 100%;" width="798" /></a><a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR5-1.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR5-1.jpg" rel="attachment wp-att-10613"><img alt="STR5" class="alignnone size-full wp-image-10613" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR5-1.jpg" height="530" src="http://www.allfordrugs.com/wp-content/uploads/2018/03/STR5-1.jpg" style="height: auto; max-width: 100%;" width="802" /></a><br />
11B NMR (128 MHz, CDCl3) δ (ppm) = 22.5.</div>
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////////////hydroboration</div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-66393590619603858402018-02-01T20:12:00.000+05:302018-02-01T20:16:28.577+05:30Guest blogger, Dr Pravin Patil, Aryl free radical mediated oxidative arylation of naphthoquinones using o-iodoxybenzoic acid and phenylhydrazines and its application towards synthesis of benzocarbazoledione<div dir="ltr" style="text-align: left;" trbidi="on">
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<span style="color: red; font-style: italic;">J. Org. Chem</span><span style="color: red;">. </span><span style="color: red; font-weight: bold;">2014</span><span style="color: red;">, </span><span style="color: red; font-style: italic;">79</span><span style="color: red;"> (5), 2331-2336 ; </span><span style="color: #00b0f0; font-family: "calibri"; font-weight: bold;">DOI: </span><span style="color: #00b0f0; font-family: "calibri";">10.1021/jo500131h</span><br />
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<span style="color: #00b0f0; font-family: "calibri";">2-Phenyl-1,4-naphthoquinone 3a.
22 Following the general
procedure, the crude product was purified over a silica gel column
using a hexane/EtOAc mobile phase (9:1) to give a yellowish solid
(140 mg, 60% yield): mp 107−109 °C; 1
H NMR (300 MHz, CDCl3)
δ 8.18−8.10 (m, 2H), 7.86−7.75 (m, 2H), 7.56−7.48 (m, 5H), 7.07 (s,
1H); 13C NMR (75 MHz, CDCl3) δ 185.2, 185.1, 148.1, 135.2, 133.9 2-Phenyl-1,4-naphthoquinone 3a.
22 Following the general
procedure, the crude product was purified over a silica gel column
using a hexane/EtOAc mobile phase (9:1) to give a yellowish solid
(140 mg, 60% yield): mp 107−109 °C; 1
H NMR (300 MHz, CDCl3)
δ 8.18−8.10 (m, 2H), 7.86−7.75 (m, 2H), 7.56−7.48 (m, 5H), 7.07 (s,
1H); 13C NMR (75 MHz, CDCl3) δ 185.2, 185.1, 148.1, 135.2, 133.9</span><br />
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CONCLUSION</div>
<div style="background-color: white; border: 0px; font-family: Arial, Helvetica, sans-serif; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
<span style="font-family: "times new roman"; font-size: 18pt;">In conclusion, we demonstrated a
new method for radical mediated arylation of naphthoquinones using the
combination of IBX with arylhydrazines. It does not require necessity of
transition metal catalysis and prefunctionalization on naphthoquinone moiety.
The reactions occurred under mild conditions in open atmosphere. Further, both
2-hydroxy and 2-amino groups were found to be tolerated under optimized
reaction conditions. This fact could be attributed to rapid reaction between
IBX and phenyl hydrazine. A postulated radical mediated mechanism was supported
by radical trapping experiments. Developed protocols were successfully extended
towards an effective, short and high yielding synthesis of benzocarbazoledione.
IBX mediated developed protocols for arylation could open a new field in
quinone chemistry as well as in the development of new procedures for arylation
of electron deficient molecules in near future</span></div>
<h1 class="articleTitle" style="background-color: white; font-family: Helvetica, Arial, sans-serif; font-size: 20px; margin-top: 0px;">
<span class="hlFld-Title">Aryl-Free Radical-Mediated Oxidative Arylation of Naphthoquinones Using <i>o</i>-Iodoxybenzoic Acid and Phenylhydrazines and Its Application toward the Synthesis of Benzocarbazoledione</span></h1>
<div id="articleMeta" style="background-color: white; line-height: 1.3em; margin-bottom: 30px; margin-top: 15px;">
<div id="authors" style="color: #333333; font-family: Helvetica, Arial, sans-serif; font-size: 1em; font-weight: bold;">
<span class="hlFld-ContribAuthor" style="white-space: nowrap;"><span class="hlFld-ContribAuthor" style="white-space: normal;"><a href="http://pubs.acs.org/author/Patil%2C+Pravin" id="authors" style="border-bottom: 1px dotted rgb(51, 102, 153); font-size: 1em; text-decoration-line: none;">Pravin Patil</a></span>, </span><span class="hlFld-ContribAuthor" style="white-space: nowrap;"><span class="hlFld-ContribAuthor" style="white-space: normal;"><a href="http://pubs.acs.org/author/Nimonkar%2C+Abhay" id="authors" style="border-bottom: 1px dotted rgb(51, 102, 153); font-size: 1em; text-decoration-line: none;">Abhay Nimonkar</a></span>, and </span><span class="hlFld-ContribAuthor" style="white-space: nowrap;"><span class="hlFld-ContribAuthor" style="white-space: normal;"><a href="http://pubs.acs.org/author/Akamanchi%2C+Krishnacharya+G" id="authors" style="border-bottom: 1px dotted rgb(51, 102, 153); font-size: 1em; text-decoration-line: none;">Krishnacharya G. Akamanchi</a></span><a class="ref" href="http://pubs.acs.org/doi/abs/10.1021/jo500131h#cor1" style="color: #336699; text-decoration-line: none;">*</a></span></div>
<div class="affiliations" style="font-family: Helvetica, Arial, sans-serif; font-size: 13px;">
<div id="aff1">
Department of Pharmaceutical Sciences and Technology, <span class="institution">Institute of Chemical Technology</span>, Matunga, Mumbai 400019, <span class="country">India</span></div>
</div>
<div id="citation" style="font-family: Helvetica, Arial, sans-serif; font-size: 0.9em; margin: 10px 0px 0px;">
<cite>J. Org. Chem.</cite>, <span class="citation_year" style="font-weight: bold;">2014</span>, <span class="citation_volume" style="font-style: italic;">79</span> (5), pp 2331–2336</div>
<div id="doi" style="font-family: Helvetica, Arial, sans-serif; font-size: 0.9em;">
<strong>DOI: </strong>10.1021/jo500131h</div>
<div id="pubDate" style="font-family: Helvetica, Arial, sans-serif; font-size: 0.9em;">
Publication Date (Web): February 10, 2014</div>
<div id="artCopyright" style="font-family: Helvetica, Arial, sans-serif; font-size: 0.9em; font-weight: bold;">
Copyright © 2014 American Chemical Society</div>
<div id="correspondence" style="color: #666666; font-family: Helvetica, Arial, sans-serif; font-size: 0.9em; margin: 7px 0px 0px; width: auto;">
*E-mail: <a href="mailto:kgap@rediffmail.com" style="color: #336699; text-decoration-line: none;">kgap@rediffmail.com</a>; <a href="mailto:kg.akamanchi@ictmumbai.edu.in" style="color: #336699; text-decoration-line: none;">kg.akamanchi@ictmumbai.edu.in</a>.</div>
<div id="correspondence" style="margin: 7px 0px 0px; width: auto;">
<span style="color: #666666; font-family: "helvetica" , "arial" , sans-serif;"><span style="font-size: 11.7px;"><a href="http://pubs.acs.org/doi/suppl/10.1021/jo500131h">http://pubs.acs.org/doi/suppl/10.1021/jo500131h</a></span></span></div>
</div>
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<div class="hlFld-Abstract">
<h2 id="Abstract" style="clear: left; color: #006ea9; font-family: "Trebuchet MS", Arial, Helvetica, sans-serif; font-size: 1.1em; font-stretch: normal; font-variant-east-asian: normal; font-variant-numeric: normal; line-height: normal; margin: 1em 0px 0px; padding: 20px 0px 3px; width: 430px;">
Abstract</h2>
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<img alt="Abstract Image" src="http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/joceah/2014/joceah.2014.79.issue-5/jo500131h/production/images/medium/jo-2014-00131h_0010.gif" style="border: 0px; max-width: 100%;" /></div>
<div class="articleBody_abstractText" style="line-height: 1.6em; margin-bottom: 1.5em; padding: 0pt; width: 610px; word-wrap: break-word;">
Oxidative arylation of naphthoquinones has been developed through combination of <i>o</i>-iodoxybenzoic acid with arylhydrazines under mild conditions at open atmosphere. Arylated naphthoquinones with different electronic properties were obtained in moderate to good yields. The postulated radical mediated mechanism is supported by radical trapping experiments. Developed protocol for direct arylation of naphthoquinones has been extended toward short, high yielding, and an effective synthesis of antitumor–antibiotic precursor such as benzocarbazoledione.</div>
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see…….<a href="http://oneorganichemistoneday.blogspot.in/2017/04/dr-pravin-patil.html" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;" target="_blank">http://oneorganichemistoneday.blogspot.in/2017/04/dr-pravin-patil.html</a></div>
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Dr. Pravin C Patil completed his B.Sc. (Chemistry) at ASC College Chopda (Jalgaon, Maharashtra, India) in 2001 and M.Sc. (Organic Chemistry) at SSVPS’S Science College Dhule in North Maharashtra University (Jalgaon, Maharashtra, India) in year 2003. After M.Sc. degree he was accepted for summer internship training program at Bhabha Atomic Research Center (BARC, Mumbai) in the laboratory of Prof. Subrata Chattopadhyay in Bio-organic Division. In 2003, Dr. Pravin joined to API Pharmaceutical bulk drug company, RPG Life Science (Navi Mumbai, Maharashtra, India) and worked there for two years. In 2005, he enrolled into Ph.D. (Chemistry) program at Institute of Chemical Technology (ICT), Matunga, Mumbai, aharashtra, under the supervision of Prof. K. G. Akamanchi in the department of Pharmaceutical Sciences and Technology.</div>
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After finishing Ph.D. in 2010, he joined to Pune (Maharashtra, India) based pharmaceutical industry, Lupin Research Park (LRP) in the department of process development. After spending two years at Lupin as a Research Scientist, he got an opportunity in June 2012 to pursue Postdoctoral studies at Hope College, Holland, MI, USA under the supervision of Prof. Moses Lee. During year 2012-13 he worked on total synthesis of achiral anticancer molecules Duocarmycin and its analogs. In 2014, he joined to Prof. Frederick Luzzio at the Department for Chemistry, University of Louisville, Louisville, KY, USA to pursue postdoctoral studies on NIH sponsored project “ Structure based design and synthesis of Peptidomimetics targeting P. gingivalis.</div>
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During his research experience, he has authored 23 international publications in peer reviewed journals and inventor for 4 patents.</div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-25159661739671535492017-12-21T15:44:00.001+05:302017-12-21T15:44:34.721+05:30HMF in multicomponent reactions: utilization of 5-hydroxymethylfurfural (HMF) in the Biginelli reaction<div dir="ltr" style="text-align: left;" trbidi="on">
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<a data-mce-href="http://feeds.rsc.org/~r/rss/GC/~3/165IgvksA98/C7GC03425C" href="http://feeds.rsc.org/~r/rss/GC/~3/165IgvksA98/C7GC03425C">HMF in multicomponent reactions: utilization of 5-hydroxymethylfurfural (HMF) in the Biginelli reaction</a></h4>
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<i><b>Green Chem.</b></i>, 2018, Advance Article<br /><b>DOI</b>: 10.1039/C7GC03425C, Paper</div>
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Weigang Fan, Yves Queneau, Florence Popowycz<br />The use of the renewable platform molecule 5-hydroxymethylfurfural (HMF) in the multi-component Biginelli reaction has been investigated.</div>
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<h2 class="capsule__title fixpadv--m">
HMF in multicomponent reactions: utilization of 5-hydroxymethylfurfural (HMF) in the Biginelli reaction</h2>
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<div class="article__authors">
<span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AWeigang%20Fan" href="http://pubs.rsc.org/en/results?searchtext=Author%3AWeigang%20Fan">Weigang Fan</a>,<sup>a</sup> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AYves%20Queneau" href="http://pubs.rsc.org/en/results?searchtext=Author%3AYves%20Queneau">Yves Queneau</a>*<sup>a</sup> and </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AFlorence%20Popowycz" href="http://pubs.rsc.org/en/results?searchtext=Author%3AFlorence%20Popowycz">Florence Popowycz</a>*<sup>a</sup> </span></div>
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* Corresponding authors</div>
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<sup>a</sup> Université de Lyon, INSA Lyon, ICBMS, Equipe Chimie Organique et Bioorganique, UMR 5246 CNRS, Université Lyon 1, CPE Lyon, Bâtiment Jules Verne, 20 Avenue Albert Einstein, F-69621 Villeurbanne Cedex, France<br /><b>E-mail:</b> <a data-mce-href="mailto:yves.queneau@insa-lyon.fr" href="mailto:yves.queneau@insa-lyon.fr" title="yves.queneau@insa-lyon.fr">yves.queneau@insa-lyon.fr</a>, <a data-mce-href="mailto:florence.popowycz@insa-lyon.fr" href="mailto:florence.popowycz@insa-lyon.fr" title="florence.popowycz@insa-lyon.fr">florence.popowycz@insa-lyon.fr</a></div>
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Abstract</h3>
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The use of the renewable platform molecule 5-hydroxymethylfurfural (HMF) in the multi-component Biginelli reaction has been investigated. Multicomponent reactions (MCR) using HMF offer straightforward access to novel fine chemicals. However, the peculiar reactivity and lower stability of HMF have limited its use in such strategies. In this paper, we report our results on the use of HMF in 3-component Biginelli reactions, leading in one single step to a series of functionalized dihydropyrimidinones obtained in moderate to good yields, with a broad substrate scope of 1,3-dicarbonyl compounds and urea building blocks. This is the first report on the use of HMF in this reaction. The CH<small><sub>2</sub></small>OH motif found in HMF provides useful functionalization for the target molecules, which cannot be offered by simpler aldehydes such as furfural.<br />
5-Acetyl-4-[5’-(hydroxymethyl)furan-2’-yl]-6-methyl-3,4-dihydropyrimidin-2(1H)-one (4a):</div>
<a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR1-7.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR1-7.jpg" rel="attachment wp-att-10175"><img alt="STR1" class="alignnone size-full wp-image-10175" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR1-7.jpg" height="420" src="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR1-7.jpg" style="height: auto; max-width: 100%;" width="655" /></a> <a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR2-2.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR2-2.jpg" rel="attachment wp-att-10176"><img alt="STR2" class="alignnone size-full wp-image-10176" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR2-2.jpg" height="430" src="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR2-2.jpg" style="height: auto; max-width: 100%;" width="635" /></a><br />
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Reaction time: 8 h; Global yield: 86%; (78% yield after simple filtration + additional 8% yield after purification of the filtrate by column chromatography).<br />
1H NMR (400 MHz, DMSO-d6) δ 9.22 (d, 1H, J = 1.2 Hz, H1), 7.88 (dd, 1H, J = 3.4, 1.2 Hz, H3), 6.16 (d, 1H, J = 3.1 Hz, H4’), 6.03 (d, 1H, J = 3.1 Hz, H3’), 5.27 (d, 1H, J = 3.4 Hz, H4), 5.18 (t, 1H, J = 5.6 Hz, OH), 4.33 (d, 2H, J = 5.6 Hz, CH2), 2.25 (s, 3H, CH3-C6), 2.17 (s, 3H, CH3CO).<br />
13C NMR (100 MHz, DMSO-d6) δ 193.9 (COCH3), 155.1, 154.9 (C2’, C5’), 152.4 (C2), 149.0 (C6), 107.7 (C4’), 107.1 (C5), 106.3 (C3’), 55.7 (CH2OH), 47.9 (C4), 30.0 (CH3CO), 19.0 (CH3-C6).<br />
HRMS (ESI) m/z: Calcd for [M+Na]+ C12H14N2NaO4 273.0846; Found 273.0850.<br />
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<a data-mce-href="https://www.researchgate.net/profile/Weigang_Fan" href="https://www.researchgate.net/profile/Weigang_Fan">Weigang Fan</a></h1>
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Research experience</h2>
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Sep 2015–Mar 2017</div>
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Doctorant</h5>
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Institut National des Sciences Appliquées de Lyon · Institut de Chimie et de Biochimie Moléculaires et Supramoléculaires (ICBMS - UMR 5246)</div>
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France · Lyon</div>
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<img alt="Image result for Florence Popowycz lyon" class="" data-mce-src="http://sites.unice.fr/site/tarrade/NICE2016/images/Keynotes/Popowycz.png" height="765" src="http://sites.unice.fr/site/tarrade/NICE2016/images/Keynotes/Popowycz.png" style="height: auto; max-width: 100%;" width="576" /></div>
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<a data-mce-href="http://www.icbms.fr/cob" href="http://www.icbms.fr/cob" target="_blank"><strong>Florence POPOWYCZ</strong></a></div>
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Université de Lyon, INSA Lyon, ICBMS, Equipe Chimie Organique et Bioorganique, UMR 5246 CNRS, Université Lyon 1, CPE Lyon, Bâtiment Jules Verne, 20 Avenue Albert Einstein, F-69621 Villeurbanne Cedex, France<br /><b>E-mail:</b> <a data-mce-href="mailto:florence.popowycz@insa-lyon.fr" href="mailto:florence.popowycz@insa-lyon.fr" title="florence.popowycz@insa-lyon.fr">florence.popowycz@insa-lyon.fr</a></div>
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<img alt="Image result for Yves Queneau lyon" class="" data-mce-src="https://media.licdn.com/mpr/mpr/shrinknp_200_200/p/7/000/2c7/2ae/1702703.jpg" height="471" src="https://media.licdn.com/mpr/mpr/shrinknp_200_200/p/7/000/2c7/2ae/1702703.jpg" style="height: auto; max-width: 100%;" width="471" /></div>
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<h1 class="pv-top-card-section__name Sans-26px-black-85%">
Yves QUENEAU</h1>
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CNRS Research Director chez ICBMS INSA Lyon Univ Lyon - Carbohydrate Chemistry</div>
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ICBMS INSA Lyon University of Lyon</h3>
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Université de Lyon, INSA Lyon, ICBMS, Equipe Chimie Organique et Bioorganique, UMR 5246 CNRS, Université Lyon 1, CPE Lyon, Bâtiment Jules Verne, 20 Avenue Albert Einstein, F-69621 Villeurbanne Cedex, France<br /><b>E-mail:</b> <a data-mce-href="mailto:yves.queneau@insa-lyon.fr" href="mailto:yves.queneau@insa-lyon.fr" title="yves.queneau@insa-lyon.fr">yves.queneau@insa-lyon.fr</a>,</div>
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<a data-mce-href="http://www.rsc.org/suppdata/c7/gc/c7gc03425c/c7gc03425c1.pdf" href="http://www.rsc.org/suppdata/c7/gc/c7gc03425c/c7gc03425c1.pdf">/////////</a>//////<a data-mce-href="http://feeds.rsc.org/~r/rss/GC/~3/165IgvksA98/C7GC03425C" href="http://feeds.rsc.org/~r/rss/GC/~3/165IgvksA98/C7GC03425C">HMF, multicomponent reactions, 5-hydroxymethylfurfural, Biginelli reaction</a></div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-43057703841238573792017-12-06T16:49:00.001+05:302017-12-06T16:49:09.785+05:30Persulfurated Coronene: A New Generation of “Sulflower”<div dir="ltr" style="text-align: left;" trbidi="on">
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<a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR1-2.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR1-2.jpg" rel="attachment wp-att-10093"><img alt="STR1" class="alignnone wp-image-10093" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR1-2.jpg" height="335" src="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR1-2.jpg" style="height: auto; max-width: 100%;" width="403" /></a></div>
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<a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR1-4.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR1-4.jpg" rel="attachment wp-att-10096"><img alt="STR1" class="alignnone size-full wp-image-10096" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR1-4.jpg" height="370" src="http://www.allfordrugs.com/wp-content/uploads/2017/12/STR1-4.jpg" style="height: auto; max-width: 100%;" width="352" /></a></div>
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2073844-77-4</div>
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<div class="molecularFormula">
C<sub>24</sub> S<sub>12, 673.04</sub></div>
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Coroneno[1,12-<em>cd</em>:2,3-<em>c</em>'<em>d</em>':4,5-<em>c</em>''<em>d</em>'':6,7-<em>c</em>'''<em>d</em>''':8,9-<em>c</em>''''<em>d</em>'''':10,11-<em>c</em>'''''<em>d</em>''''']hexakis[1,2]dithiole</div>
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A persulfurated coronene, a molecule dubbed a “sulflower” for its resemblance to a sunflower, bloomed this year. It’s the first fully sulfur-substituted polycyclic aromatic hydrocarbon and only the second member of a new class of circular heterocyclic carbon sulfide compounds, after the synthesis of <a data-mce-href="http://cen.acs.org/articles/84/i43/Sulflowercirculene-debuts.html" href="http://cen.acs.org/articles/84/i43/Sulflowercirculene-debuts.html" title="‘Sulflower’ circulene debuts">octathio[8]circulene</a> a decade ago.</div>
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Chemists hope to create other class members, including the simplest one, persulfurated benzene, for use in battery cathodes and other electronic materials.</div>
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A team led by Xinliang Feng of Dresden University of Technology and Klaus Müllen of the Max Planck Institute for Polymer Research created the sulflower (<i>J. Am. Chem. Soc.</i> 2017, <a data-mce-href="http://cgi.cen.acs.org/cgi-bin/cen/trustedproxy.cgi?redirect=http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630?source=cen" href="http://cgi.cen.acs.org/cgi-bin/cen/trustedproxy.cgi?redirect=http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630?source=cen" title="Persulfurated Coronene: A New Generation of “Sulflower”">DOI: 10.1021/jacs.6b12630</a>).</div>
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<a data-mce-href="http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630" href="http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630">http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630</a></div>
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Synthesis of persulfuratedcoronene (5, PSC)</div>
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5 (82 mg) as dark red solid in 61% yield. HR-MS (HR-MALDI-TOF) m/z: Calcd. for C24S12: 671.6629; Found 671.6648 [M]+; Elem. Anal. calcd. for C24S12: C, 42.83; S, 57.17. Found: C, 42.87; S, 57.13.</div>
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<h1 class="articleTitle" style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif;">
<span class="hlFld-Title">Persulfurated Coronene: A New Generation of “Sulflower”</span></h1>
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<span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Dong%2C+Renhao" href="http://pubs.acs.org/author/Dong%2C+Renhao" id="authors">Renhao Dong</a></span><span class="NLM_xref-aff"><sup>†</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Pfeffermann%2C+Martin" href="http://pubs.acs.org/author/Pfeffermann%2C+Martin" id="authors">Martin Pfeffermann</a></span><span class="NLM_xref-aff"><sup>§</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Skidin%2C+Dmitry" href="http://pubs.acs.org/author/Skidin%2C+Dmitry" id="authors">Dmitry Skidin</a></span><span class="NLM_xref-aff"><sup>‡</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Wang%2C+Faxing" href="http://pubs.acs.org/author/Wang%2C+Faxing" id="authors">Faxing Wang</a></span><span class="NLM_xref-aff"><sup>†</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Fu%2C+Yubin" href="http://pubs.acs.org/author/Fu%2C+Yubin" id="authors">Yubin Fu</a></span><span class="NLM_xref-aff"><sup>†</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Narita%2C+Akimitsu" href="http://pubs.acs.org/author/Narita%2C+Akimitsu" id="authors">Akimitsu Narita</a></span><span class="NLM_xref-aff"><sup>§</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Tommasini%2C+Matteo" href="http://pubs.acs.org/author/Tommasini%2C+Matteo" id="authors">Matteo Tommasini</a></span><span class="NLM_xref-aff"><sup>∥</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Moresco%2C+Francesca" href="http://pubs.acs.org/author/Moresco%2C+Francesca" id="authors">Francesca Moresco</a></span><span class="NLM_xref-aff"><sup>‡</sup></span><span class="orcid-link-icon"> <a data-mce-href="http://orcid.org/0000-0001-9607-8715" href="http://orcid.org/0000-0001-9607-8715" target="_blank"><img alt="" data-mce-src="http://pubs.acs.org/templates/jsp/images/orcid.png" src="http://pubs.acs.org/templates/jsp/images/orcid.png" style="height: auto; max-width: 100%;" /></a></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Cuniberti%2C+Gianaurelio" href="http://pubs.acs.org/author/Cuniberti%2C+Gianaurelio" id="authors">Gianaurelio Cuniberti</a></span><span class="NLM_xref-aff"><sup>‡</sup></span><span class="orcid-link-icon"> <a data-mce-href="http://orcid.org/0000-0002-6574-7848" href="http://orcid.org/0000-0002-6574-7848" target="_blank"><img alt="" data-mce-src="http://pubs.acs.org/templates/jsp/images/orcid.png" src="http://pubs.acs.org/templates/jsp/images/orcid.png" style="height: auto; max-width: 100%;" /></a></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Berger%2C+Reinhard" href="http://pubs.acs.org/author/Berger%2C+Reinhard" id="authors">Reinhard Berger</a></span><span class="NLM_xref-aff"><sup>†</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/M%C3%BCllen%2C+Klaus" href="http://pubs.acs.org/author/M%C3%BCllen%2C+Klaus" id="authors">Klaus Müllen</a></span><a class="ref" data-mce-href="http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630?source=chemport#cor1" href="http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630?source=chemport#cor1"><sup>*</sup></a><span class="NLM_xref-aff"><sup>§</sup></span><span class="orcid-link-icon"> <a data-mce-href="http://orcid.org/0000-0001-6630-8786" href="http://orcid.org/0000-0001-6630-8786" target="_blank"><img alt="" data-mce-src="http://pubs.acs.org/templates/jsp/images/orcid.png" src="http://pubs.acs.org/templates/jsp/images/orcid.png" style="height: auto; max-width: 100%;" /></a></span>, and </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Feng%2C+Xinliang" href="http://pubs.acs.org/author/Feng%2C+Xinliang" id="authors">Xinliang Feng</a></span><a class="ref" data-mce-href="http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630?source=chemport#cor2" href="http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630?source=chemport#cor2"><sup>*</sup></a><span class="NLM_xref-aff"><sup>†</sup></span></span></div>
<div class="affiliations">
<div id="aff1">
<sup>†</sup> Department of Chemistry and Food Chemistry, Center for Advancing Electronics Dresden, <span class="institution">Technische Universität Dresden</span>, 01062 Dresden, <span class="country">Germany</span></div>
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<sup>§</sup> <span class="institution">Max-Planck-Institute for Polymer Research</span>, Ackermannweg 10, 55128 Mainz, <span class="country">Germany</span></div>
<div id="aff3">
<sup>‡</sup> Institute for Materials Science, Max Bergmann Center of Biomaterials, and Center for Advancing Electronics Dresden, <span class="institution">TU Dresden</span>, 01069 Dresden, <span class="country">Germany</span></div>
<div id="aff4">
<sup>∥</sup> Dipartimento di Chimica, Materiali ed Ingegneria Chimica ‘G. Natta’, <span class="institution">Politecnico di Milano</span>, Piazza Leonardo da Vinci 32, 20133 Milano, <span class="country">Italy</span></div>
</div>
<div id="citation">
<cite>J. Am. Chem. Soc.</cite>, <span class="citation_year">2017</span>, <span class="citation_volume">139</span> (6), pp 2168–2171</div>
<div id="doi">
<strong>DOI: </strong>10.1021/jacs.6b12630</div>
<div id="pubDate">
Publication Date (Web): January 27, 2017</div>
<div id="artCopyright">
Copyright © 2017 American Chemical Society</div>
<div id="correspondence">
*<a data-mce-href="mailto:muellen@mpip-mainz.mpg.de" href="mailto:muellen@mpip-mainz.mpg.de">muellen@mpip-mainz.mpg.de</a>, *<a data-mce-href="mailto:xinliang.feng@tu-dresden.de" href="mailto:xinliang.feng@tu-dresden.de">xinliang.feng@tu-dresden.de</a></div>
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<img alt="Abstract Image" data-mce-src="http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jacsat/2017/jacsat.2017.139.issue-6/jacs.6b12630/20170209/images/medium/ja-2016-12630p_0007.gif" src="http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jacsat/2017/jacsat.2017.139.issue-6/jacs.6b12630/20170209/images/medium/ja-2016-12630p_0007.gif" style="height: auto; max-width: 100%;" /></div>
<div class="articleBody_abstractText" style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
We report the first synthesis of a persulfurated polycyclic aromatic hydrocarbon (PAH) as a next-generation “sulflower.” In this novel PAH, disulfide units establish an all-sulfur periphery around a coronene core. The structure, electronic properties, and redox behavior were investigated by microscopic, spectroscopic and electrochemical methods and supported by density functional theory. The sulfur-rich character of persulfurated coronene renders it a promising cathode material for lithium–sulfur batteries, displaying a high capacity of 520 mAh g<sup>–1</sup> after 120 cycles at 0.6 C with a high-capacity retention of 90%</div>
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<a data-mce-href="https://tu-dresden.de/?set_language=en" href="https://tu-dresden.de/?set_language=en" target="_blank"><img alt="" class="" data-mce-src="https://cfaed.tu-dresden.de/files/themes/cfaed/img/header/logo_TUD_header.png" height="182" src="https://cfaed.tu-dresden.de/files/themes/cfaed/img/header/logo_TUD_header.png" style="height: auto; max-width: 100%;" width="628" /></a></div>
<h2 style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif;">
Renhao Dong</h2>
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<img alt="Image result for Renhao Dong DRESDEN" class="" data-mce-src="https://cfaed.tu-dresden.de/files/Images/people/chair-mfm/portrait_renhao-dong.jpg" height="554" src="https://cfaed.tu-dresden.de/files/Images/people/chair-mfm/portrait_renhao-dong.jpg" style="height: auto; max-width: 100%;" width="393" /></div>
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<strong>Research Group Leader</strong></div>
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Renhao received his PhD in Physical Chemistry from Shandong University in 2013. Since 01/2017, he is a research group leader at the Chair for Molecular Functional Materials in TUD. His current research interest focuses on synthesis of organic 2D crystals (2D polymers/COFs/MOFs) and their applications in electronics and energy technology.</div>
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Contact</h3>
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Phone: +49 – 351 / 463-40401 or -34932<br />Email: <a data-mce-href="mailto:renhao.dong@tu-dresden.de" href="mailto:renhao.dong@tu-dresden.de" title="Mail to Renhao">renhao.dong@tu-dresden.de</a></div>
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<img alt="Prof. Xinliang Feng" class="" data-mce-src="https://cfaed.tu-dresden.de/files/Images/people/chair-mfm/portret_xinliang-feng.jpg" height="760" src="https://cfaed.tu-dresden.de/files/Images/people/chair-mfm/portret_xinliang-feng.jpg" style="height: auto; max-width: 100%;" width="539" /></div>
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Prof. Xinliang Feng</h2>
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Work Biography:</h2>
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This is a professorship in the context of the cluster of excellence cfaed.</h3>
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Xinliang Feng received his Bachelor’s degree in analytic chemistry in 2001 and Master’s degree in organic chemistry in 2004. Then he joined Prof. Klaus Müllen's group at the Max Planck Institute for Polymer Research for PhD thesis, where he obtained his PhD degree in April 2008. In December 2007 he was appointed as a group leader at the Max-Planck Institute for Polymer Research and in 2012 he became a distinguished group leader at the Max-Planck Institute for Polymer Research.</div>
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His current scientific interests include graphene, two-dimensional nanomaterials, organic conjugated materials, and carbon-rich molecules and materials for electronic and energy-related applications. He has published more than 370 research articles which have attracted more than 25000 citations with H-index of 75.</div>
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He has been awarded several prestigious prizes such as IUPAC Prize for Young Chemists (2009), Finalist of 3rd European Young Chemist Award, European Research Council (ERC) Starting Grant Award (2012), Journal of Materials Chemistry Lectureship Award (2013), ChemComm Emerging Investigator Lectureship (2014), Highly Cited Researcher (Thomson Reuters, 2014, 2015 and 2016), Fellow of the Royal Society of Chemistry (FRSC, 2014). He is an Advisory Board Member for Advanced Materials, Journal of Materials Chemistry A, ChemNanoMat, Energy Storage Materials, Small Methods and Chemistry -An Asian Journal. He is also one of the Deputy Leaders for European communitys pilot project Graphene Flagship, Head of ESF Young Research Group "Graphene Center Dresden", and Working Package Leader of WP Functional Foams & Coatings of GRAPHENE FLAGSHIP.</div>
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Academic Employment</h2>
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<li>12/2007-12/2012: Group Leader, Max Planck Institute for Polymer Research in Mainz, Germany</li>
<li>06/2010: Director of the Institute of Advanced Organic Materials, Shanghai Jiao Tong University</li>
<li>03/2011: Distinguished Adjunct Professorship in Shanghai Jiao Tong University, Chin</li>
<li>12/2012-07/2014: Distinguished Group Leader, Max Planck Institute for Polymer Research in Mainz, Germany</li>
<li>08/2014: W3 Chair Professor, Technische Universität Dresden, Germany</li>
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Honors and Duties</h2>
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<li>Marie Currie Fellowship (2005-2006)</li>
<li>Chinese Government Award for Outstanding Self-financed Students (2008)</li>
<li>IUPAC Prize for Young Chemists (2009)</li>
<li>Finalist of 3rd European Young Chemist Award (2010)</li>
<li>ISE (International Society of Electrochemistry) Young Investigator Award (2011)</li>
<li>Adjunct Professorship, China University of Geosciences (Wuhan) (2011)</li>
<li>Deputy Leader of one of the ten European representatives of the European community’s pilot project GRAPHENE FLAGSHIP (2012)</li>
<li>EU FET Young Explorer (2012)</li>
<li>ERC Starting Grant Award (2012)</li>
<li>Advisory Board Member for Advanced Materials (2013)</li>
<li>Journal of Materials Chemistry Lectureship Award (2013)</li>
<li>Advisory Board Member for Journal of Materials Chemistry A (2014)</li>
<li>Editorial Board Member of Chemistry - An Asian Journal (2014)</li>
<li>ChemComm Emerging Investigator Lectureship (2014)</li>
<li>Highly Cited Researcher (Thomson Reuters, 2014)</li>
<li>Fellow of the Royal Society of Chemistry (2014)</li>
<li>Highly Cited Researcher (Chemistry and Materials Science) (2015)</li>
<li>International Advisory Board of Energy Storage Materials (2015)</li>
<li>International Advisory Board of ChemNanoMat (2015)</li>
<li>Highly Cited Researcher (Chemistry and Materials Science, Thomson Reuters) (2016)</li>
<li>Head of ESF Young Research Group “Graphene Center Dresden” (2016)</li>
<li>Working Package Leader of WP Functional Foams & Coatings of GRAPHENE FLAGSHIP (2016)</li>
<li>International Advisory Board of Small Methods (2016)</li>
<li>Path Leader of 2.5D path within the cluster of excellence CFAED (2016)</li>
<li>ERC Proof-of-Concept Project Award (2017)</li>
<li><em>Small</em> Young Innovator Award (2017)</li>
<li>Hamburg Science Award (2017)</li>
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Referee for:</h2>
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Nature, Science, Nature Materials, Nature Nanotechnology, Nature Chemistry, Journal of the American Chemical Society, Angewandte Chemie International Edition, Nano Letters, Advanced Materials, Chemical Society Reviews, ACS Nano, Small, Chemical Communications, Chemistry of Materials, Organic Letters, Journal of the Organic Chemistry, Chemistry - A European Journal, ChemSusChem, ChemPhysChem, Macromolecular Rapid Communications, Journal of Material Chemistry, New Journal of Chemistry, Chemistry - An Asian Journal, ACS Applied Materials & Interfaces, Energy & Environmental Science, Organic Electronics and so on</div>
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Referee for research grants in NSF, US Department of Energy, ESF, ISF and Fondazione Cariparo and Fondazione CariModena.</div>
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Publications</h2>
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<a data-mce-href="https://cfaed.tu-dresden.de/cmfm-publications" href="https://cfaed.tu-dresden.de/cmfm-publications">Click to open publications list</a></div>
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Contact (Secretariat)</h2>
<div style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
Phone: +49 351 / 463-43251<br />Fax: +49 351 / 463-43268<br />Email: <a data-mce-href="mailto:sabine.strecker@tu-dresden.de" href="mailto:sabine.strecker@tu-dresden.de" title="Mail to Sabine">sabine.strecker@tu-dresden.de</a></div>
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<b>Klaus Müllen</b><br /><i>Max-Planck-Institute for Polymer Research, Mainz, 55128, Germany</i></center>
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<a href="https://www.blogger.com/null" title="vyrez_DSC_3783.JPG"><img alt="vyrez_DSC_3783.JPG" border="0" class="" data-mce-src="http://www.jh-inst.cas.cz/www/data/lecture/obrazek/119.jpg" height="544" hspace="4" src="http://www.jh-inst.cas.cz/www/data/lecture/obrazek/119.jpg" style="height: auto; max-width: 100%;" vspace="2" width="408" /></a></div>
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Research into energy technologies and electronic devices is strongly governed by the available materials. We introduce a synthetic route to graphenes which is based upon the cyclodehydrogenation (“graphitization”) of well-defined dendritic (3D) polyphenylene precursors. This approach is superior to physical methods of graphene formation such as chemical vapour deposition or exfoliation in terms of its (i) size and shape control, (ii) structural perfection, and (iii) processability (solution, melt, and even gas phase). The most convincing case is the synthesis of graphene nanoribbons under surface immobilization and in-situ control by scanning tunnelling microscopy.<br />Columnar superstructures assembled from these nanographene discs serve as charge transport channels in electronic devices. Field-effect transistors (FETs), solar cells, and sensors are described as examples.<br />Upon pyrolysis in confining geometries or “carbomesophases”, the above carbon-rich 2D- and 3D- macromolecules transform into unprecedented carbon materials and their carbon-metal nanocomposites. Exciting applications are shown for energy technologies such as battery cells and fuel cells. In the latter case, nitrogen-containing graphenes serve as catalysts for oxygen reduction whose efficiency is superior to that of platinum.</div>
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<i>Müllen, K., Rabe, J.R., Acc. Chem. Res. 2008, 41, (4), 511-520;<br />Wang, X., Zhi, L., Müllen, K. Nano. Lett. 2008, 8, 323-327;<br />Feng, X.; Chandrasekhar, N.; Su, H. B.; Müllen, K., Nano. Lett. 2008, 8, 4259.;<br />Pang, S.; Tsao, H. N.; Feng, X.; Müllen, K., Adv. Mater. 2009, 31, 3488;<br />Feng, X., Marcon, V., Pisula, W., Hansen, M.R., Kirkpatrick, I., Müllen, K., Nature Mater. 2009, 8, 421;<br />Cai, J., Ruffieux, P., Jaafar, R., Bieri, M., Braun, T., Blankenburg, S., Muoth, M., Seitsonen, A. P., Saleh, M., Feng, X., Müllen, K., Fasel, R., Nature 2010, 466, 470-473;<br />Yang, S., Feng, X., Zhi, L., Cao, Q., Maier, J., Müllen, K., Adv. Mater. 2010, 22, 838; Liu, R., Wu, D., Feng, X., Müllen, K., Angew. Chem. Int. Ed. 2010, 49, 2565;<br />Käfer, D., Bashir, A., Dou, X., Witte, G., Müllen, K., Wöll, C., Adv. Mater. 2010, 22, 384;<br />Diez-Perez, I., Li, Z., Hihath, J., Li, J., Zhang, C., X., Zang, L., Dai, Y., Heng, X., Müllen, K., Tao, N. J. Nature Commun. 2010, DOI: 10.1038.</i></div>
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<i>Prof. Dr. Klaus Müllen<br />joined the Max-Planck-Society in 1989 as one of the directors of the Max-Planck Institute for Polymer Research. He obtained a Diplom-Chemiker degree at the University of Cologne in 1969 after work with Professor E. Vogel. His Ph.D. degree was granted by the University of Basel, Switzerland, in 1972 where he undertook research with Professor F. Gerson on twisted pi-systems and EPR spectroscopic properties of the corresponding radical anions. In 1972 he joined the group of Professor J.F.M. Oth at the Swiss Federal Institute of Technology in Zürich where he worked in the field of dynamic NMR spectroscopy and electrochemistry. He received his habilitation from the ETH Zürich in 1977 and was appointed Privatdozent. In 1979 he became a Professor in the Department of Organic Chemistry, University of Cologne, and accepted an offer of a chair in Organic Chemistry at the University of Mainz in 1983. He received a call to the University of Göttingen in 1988.</i></div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-80754277703731227062017-12-06T16:48:00.001+05:302017-12-06T16:48:33.460+05:30Persulfurated Coronene: A New Generation of “Sulflower”<div dir="ltr" style="text-align: left;" trbidi="on">
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2073844-77-4</div>
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<div class="molecularFormula">
C<sub>24</sub> S<sub>12, 673.04</sub></div>
<div class="indexName">
Coroneno[1,12-<em>cd</em>:2,3-<em>c</em>'<em>d</em>':4,5-<em>c</em>''<em>d</em>'':6,7-<em>c</em>'''<em>d</em>''':8,9-<em>c</em>''''<em>d</em>'''':10,11-<em>c</em>'''''<em>d</em>''''']hexakis[1,2]dithiole</div>
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A persulfurated coronene, a molecule dubbed a “sulflower” for its resemblance to a sunflower, bloomed this year. It’s the first fully sulfur-substituted polycyclic aromatic hydrocarbon and only the second member of a new class of circular heterocyclic carbon sulfide compounds, after the synthesis of <a data-mce-href="http://cen.acs.org/articles/84/i43/Sulflowercirculene-debuts.html" href="http://cen.acs.org/articles/84/i43/Sulflowercirculene-debuts.html" title="‘Sulflower’ circulene debuts">octathio[8]circulene</a> a decade ago.</div>
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Chemists hope to create other class members, including the simplest one, persulfurated benzene, for use in battery cathodes and other electronic materials.</div>
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A team led by Xinliang Feng of Dresden University of Technology and Klaus Müllen of the Max Planck Institute for Polymer Research created the sulflower (<i>J. Am. Chem. Soc.</i> 2017, <a data-mce-href="http://cgi.cen.acs.org/cgi-bin/cen/trustedproxy.cgi?redirect=http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630?source=cen" href="http://cgi.cen.acs.org/cgi-bin/cen/trustedproxy.cgi?redirect=http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630?source=cen" title="Persulfurated Coronene: A New Generation of “Sulflower”">DOI: 10.1021/jacs.6b12630</a>).</div>
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<a data-mce-href="http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630" href="http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630">http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630</a></div>
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Synthesis of persulfuratedcoronene (5, PSC)</div>
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5 (82 mg) as dark red solid in 61% yield. HR-MS (HR-MALDI-TOF) m/z: Calcd. for C24S12: 671.6629; Found 671.6648 [M]+; Elem. Anal. calcd. for C24S12: C, 42.83; S, 57.17. Found: C, 42.87; S, 57.13.</div>
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<h1 class="articleTitle" style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif;">
<span class="hlFld-Title">Persulfurated Coronene: A New Generation of “Sulflower”</span></h1>
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<div id="authors">
<span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Dong%2C+Renhao" href="http://pubs.acs.org/author/Dong%2C+Renhao" id="authors">Renhao Dong</a></span><span class="NLM_xref-aff"><sup>†</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Pfeffermann%2C+Martin" href="http://pubs.acs.org/author/Pfeffermann%2C+Martin" id="authors">Martin Pfeffermann</a></span><span class="NLM_xref-aff"><sup>§</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Skidin%2C+Dmitry" href="http://pubs.acs.org/author/Skidin%2C+Dmitry" id="authors">Dmitry Skidin</a></span><span class="NLM_xref-aff"><sup>‡</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Wang%2C+Faxing" href="http://pubs.acs.org/author/Wang%2C+Faxing" id="authors">Faxing Wang</a></span><span class="NLM_xref-aff"><sup>†</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Fu%2C+Yubin" href="http://pubs.acs.org/author/Fu%2C+Yubin" id="authors">Yubin Fu</a></span><span class="NLM_xref-aff"><sup>†</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Narita%2C+Akimitsu" href="http://pubs.acs.org/author/Narita%2C+Akimitsu" id="authors">Akimitsu Narita</a></span><span class="NLM_xref-aff"><sup>§</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Tommasini%2C+Matteo" href="http://pubs.acs.org/author/Tommasini%2C+Matteo" id="authors">Matteo Tommasini</a></span><span class="NLM_xref-aff"><sup>∥</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Moresco%2C+Francesca" href="http://pubs.acs.org/author/Moresco%2C+Francesca" id="authors">Francesca Moresco</a></span><span class="NLM_xref-aff"><sup>‡</sup></span><span class="orcid-link-icon"> <a data-mce-href="http://orcid.org/0000-0001-9607-8715" href="http://orcid.org/0000-0001-9607-8715" target="_blank"><img alt="" data-mce-src="http://pubs.acs.org/templates/jsp/images/orcid.png" src="http://pubs.acs.org/templates/jsp/images/orcid.png" style="height: auto; max-width: 100%;" /></a></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Cuniberti%2C+Gianaurelio" href="http://pubs.acs.org/author/Cuniberti%2C+Gianaurelio" id="authors">Gianaurelio Cuniberti</a></span><span class="NLM_xref-aff"><sup>‡</sup></span><span class="orcid-link-icon"> <a data-mce-href="http://orcid.org/0000-0002-6574-7848" href="http://orcid.org/0000-0002-6574-7848" target="_blank"><img alt="" data-mce-src="http://pubs.acs.org/templates/jsp/images/orcid.png" src="http://pubs.acs.org/templates/jsp/images/orcid.png" style="height: auto; max-width: 100%;" /></a></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Berger%2C+Reinhard" href="http://pubs.acs.org/author/Berger%2C+Reinhard" id="authors">Reinhard Berger</a></span><span class="NLM_xref-aff"><sup>†</sup></span>, </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/M%C3%BCllen%2C+Klaus" href="http://pubs.acs.org/author/M%C3%BCllen%2C+Klaus" id="authors">Klaus Müllen</a></span><a class="ref" data-mce-href="http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630?source=chemport#cor1" href="http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630?source=chemport#cor1"><sup>*</sup></a><span class="NLM_xref-aff"><sup>§</sup></span><span class="orcid-link-icon"> <a data-mce-href="http://orcid.org/0000-0001-6630-8786" href="http://orcid.org/0000-0001-6630-8786" target="_blank"><img alt="" data-mce-src="http://pubs.acs.org/templates/jsp/images/orcid.png" src="http://pubs.acs.org/templates/jsp/images/orcid.png" style="height: auto; max-width: 100%;" /></a></span>, and </span><span class="hlFld-ContribAuthor"><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Feng%2C+Xinliang" href="http://pubs.acs.org/author/Feng%2C+Xinliang" id="authors">Xinliang Feng</a></span><a class="ref" data-mce-href="http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630?source=chemport#cor2" href="http://pubs.acs.org/doi/abs/10.1021/jacs.6b12630?source=chemport#cor2"><sup>*</sup></a><span class="NLM_xref-aff"><sup>†</sup></span></span></div>
<div class="affiliations">
<div id="aff1">
<sup>†</sup> Department of Chemistry and Food Chemistry, Center for Advancing Electronics Dresden, <span class="institution">Technische Universität Dresden</span>, 01062 Dresden, <span class="country">Germany</span></div>
<div id="aff2">
<sup>§</sup> <span class="institution">Max-Planck-Institute for Polymer Research</span>, Ackermannweg 10, 55128 Mainz, <span class="country">Germany</span></div>
<div id="aff3">
<sup>‡</sup> Institute for Materials Science, Max Bergmann Center of Biomaterials, and Center for Advancing Electronics Dresden, <span class="institution">TU Dresden</span>, 01069 Dresden, <span class="country">Germany</span></div>
<div id="aff4">
<sup>∥</sup> Dipartimento di Chimica, Materiali ed Ingegneria Chimica ‘G. Natta’, <span class="institution">Politecnico di Milano</span>, Piazza Leonardo da Vinci 32, 20133 Milano, <span class="country">Italy</span></div>
</div>
<div id="citation">
<cite>J. Am. Chem. Soc.</cite>, <span class="citation_year">2017</span>, <span class="citation_volume">139</span> (6), pp 2168–2171</div>
<div id="doi">
<strong>DOI: </strong>10.1021/jacs.6b12630</div>
<div id="pubDate">
Publication Date (Web): January 27, 2017</div>
<div id="artCopyright">
Copyright © 2017 American Chemical Society</div>
<div id="correspondence">
*<a data-mce-href="mailto:muellen@mpip-mainz.mpg.de" href="mailto:muellen@mpip-mainz.mpg.de">muellen@mpip-mainz.mpg.de</a>, *<a data-mce-href="mailto:xinliang.feng@tu-dresden.de" href="mailto:xinliang.feng@tu-dresden.de">xinliang.feng@tu-dresden.de</a></div>
</div>
<div id="absImg" style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
<img alt="Abstract Image" data-mce-src="http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jacsat/2017/jacsat.2017.139.issue-6/jacs.6b12630/20170209/images/medium/ja-2016-12630p_0007.gif" src="http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jacsat/2017/jacsat.2017.139.issue-6/jacs.6b12630/20170209/images/medium/ja-2016-12630p_0007.gif" style="height: auto; max-width: 100%;" /></div>
<div class="articleBody_abstractText" style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
We report the first synthesis of a persulfurated polycyclic aromatic hydrocarbon (PAH) as a next-generation “sulflower.” In this novel PAH, disulfide units establish an all-sulfur periphery around a coronene core. The structure, electronic properties, and redox behavior were investigated by microscopic, spectroscopic and electrochemical methods and supported by density functional theory. The sulfur-rich character of persulfurated coronene renders it a promising cathode material for lithium–sulfur batteries, displaying a high capacity of 520 mAh g<sup>–1</sup> after 120 cycles at 0.6 C with a high-capacity retention of 90%</div>
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<a data-mce-href="https://tu-dresden.de/?set_language=en" href="https://tu-dresden.de/?set_language=en" target="_blank"><img alt="" class="" data-mce-src="https://cfaed.tu-dresden.de/files/themes/cfaed/img/header/logo_TUD_header.png" height="182" src="https://cfaed.tu-dresden.de/files/themes/cfaed/img/header/logo_TUD_header.png" style="height: auto; max-width: 100%;" width="628" /></a></div>
<h2 style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif;">
Renhao Dong</h2>
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<img alt="Image result for Renhao Dong DRESDEN" class="" data-mce-src="https://cfaed.tu-dresden.de/files/Images/people/chair-mfm/portrait_renhao-dong.jpg" height="554" src="https://cfaed.tu-dresden.de/files/Images/people/chair-mfm/portrait_renhao-dong.jpg" style="height: auto; max-width: 100%;" width="393" /></div>
<div style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
<strong>Research Group Leader</strong></div>
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Renhao received his PhD in Physical Chemistry from Shandong University in 2013. Since 01/2017, he is a research group leader at the Chair for Molecular Functional Materials in TUD. His current research interest focuses on synthesis of organic 2D crystals (2D polymers/COFs/MOFs) and their applications in electronics and energy technology.</div>
<h3 style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif;">
Contact</h3>
<div style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
Phone: +49 – 351 / 463-40401 or -34932<br />Email: <a data-mce-href="mailto:renhao.dong@tu-dresden.de" href="mailto:renhao.dong@tu-dresden.de" title="Mail to Renhao">renhao.dong@tu-dresden.de</a></div>
<div style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
<img alt="Prof. Xinliang Feng" class="" data-mce-src="https://cfaed.tu-dresden.de/files/Images/people/chair-mfm/portret_xinliang-feng.jpg" height="760" src="https://cfaed.tu-dresden.de/files/Images/people/chair-mfm/portret_xinliang-feng.jpg" style="height: auto; max-width: 100%;" width="539" /></div>
<h2 style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif;">
Prof. Xinliang Feng</h2>
<h2 style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif;">
Work Biography:</h2>
<h3 style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif;">
This is a professorship in the context of the cluster of excellence cfaed.</h3>
<div style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
Xinliang Feng received his Bachelor’s degree in analytic chemistry in 2001 and Master’s degree in organic chemistry in 2004. Then he joined Prof. Klaus Müllen's group at the Max Planck Institute for Polymer Research for PhD thesis, where he obtained his PhD degree in April 2008. In December 2007 he was appointed as a group leader at the Max-Planck Institute for Polymer Research and in 2012 he became a distinguished group leader at the Max-Planck Institute for Polymer Research.</div>
<div style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
His current scientific interests include graphene, two-dimensional nanomaterials, organic conjugated materials, and carbon-rich molecules and materials for electronic and energy-related applications. He has published more than 370 research articles which have attracted more than 25000 citations with H-index of 75.</div>
<div style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
He has been awarded several prestigious prizes such as IUPAC Prize for Young Chemists (2009), Finalist of 3rd European Young Chemist Award, European Research Council (ERC) Starting Grant Award (2012), Journal of Materials Chemistry Lectureship Award (2013), ChemComm Emerging Investigator Lectureship (2014), Highly Cited Researcher (Thomson Reuters, 2014, 2015 and 2016), Fellow of the Royal Society of Chemistry (FRSC, 2014). He is an Advisory Board Member for Advanced Materials, Journal of Materials Chemistry A, ChemNanoMat, Energy Storage Materials, Small Methods and Chemistry -An Asian Journal. He is also one of the Deputy Leaders for European communitys pilot project Graphene Flagship, Head of ESF Young Research Group "Graphene Center Dresden", and Working Package Leader of WP Functional Foams & Coatings of GRAPHENE FLAGSHIP.</div>
<h2 style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif;">
Academic Employment</h2>
<ul style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
<li>12/2007-12/2012: Group Leader, Max Planck Institute for Polymer Research in Mainz, Germany</li>
<li>06/2010: Director of the Institute of Advanced Organic Materials, Shanghai Jiao Tong University</li>
<li>03/2011: Distinguished Adjunct Professorship in Shanghai Jiao Tong University, Chin</li>
<li>12/2012-07/2014: Distinguished Group Leader, Max Planck Institute for Polymer Research in Mainz, Germany</li>
<li>08/2014: W3 Chair Professor, Technische Universität Dresden, Germany</li>
</ul>
<h2 style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif;">
Honors and Duties</h2>
<ul style="color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
<li>Marie Currie Fellowship (2005-2006)</li>
<li>Chinese Government Award for Outstanding Self-financed Students (2008)</li>
<li>IUPAC Prize for Young Chemists (2009)</li>
<li>Finalist of 3rd European Young Chemist Award (2010)</li>
<li>ISE (International Society of Electrochemistry) Young Investigator Award (2011)</li>
<li>Adjunct Professorship, China University of Geosciences (Wuhan) (2011)</li>
<li>Deputy Leader of one of the ten European representatives of the European community’s pilot project GRAPHENE FLAGSHIP (2012)</li>
<li>EU FET Young Explorer (2012)</li>
<li>ERC Starting Grant Award (2012)</li>
<li>Advisory Board Member for Advanced Materials (2013)</li>
<li>Journal of Materials Chemistry Lectureship Award (2013)</li>
<li>Advisory Board Member for Journal of Materials Chemistry A (2014)</li>
<li>Editorial Board Member of Chemistry - An Asian Journal (2014)</li>
<li>ChemComm Emerging Investigator Lectureship (2014)</li>
<li>Highly Cited Researcher (Thomson Reuters, 2014)</li>
<li>Fellow of the Royal Society of Chemistry (2014)</li>
<li>Highly Cited Researcher (Chemistry and Materials Science) (2015)</li>
<li>International Advisory Board of Energy Storage Materials (2015)</li>
<li>International Advisory Board of ChemNanoMat (2015)</li>
<li>Highly Cited Researcher (Chemistry and Materials Science, Thomson Reuters) (2016)</li>
<li>Head of ESF Young Research Group “Graphene Center Dresden” (2016)</li>
<li>Working Package Leader of WP Functional Foams & Coatings of GRAPHENE FLAGSHIP (2016)</li>
<li>International Advisory Board of Small Methods (2016)</li>
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<b>Klaus Müllen</b><br /><i>Max-Planck-Institute for Polymer Research, Mainz, 55128, Germany</i></center>
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Research into energy technologies and electronic devices is strongly governed by the available materials. We introduce a synthetic route to graphenes which is based upon the cyclodehydrogenation (“graphitization”) of well-defined dendritic (3D) polyphenylene precursors. This approach is superior to physical methods of graphene formation such as chemical vapour deposition or exfoliation in terms of its (i) size and shape control, (ii) structural perfection, and (iii) processability (solution, melt, and even gas phase). The most convincing case is the synthesis of graphene nanoribbons under surface immobilization and in-situ control by scanning tunnelling microscopy.<br />Columnar superstructures assembled from these nanographene discs serve as charge transport channels in electronic devices. Field-effect transistors (FETs), solar cells, and sensors are described as examples.<br />Upon pyrolysis in confining geometries or “carbomesophases”, the above carbon-rich 2D- and 3D- macromolecules transform into unprecedented carbon materials and their carbon-metal nanocomposites. Exciting applications are shown for energy technologies such as battery cells and fuel cells. In the latter case, nitrogen-containing graphenes serve as catalysts for oxygen reduction whose efficiency is superior to that of platinum.</div>
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<i>Müllen, K., Rabe, J.R., Acc. Chem. Res. 2008, 41, (4), 511-520;<br />Wang, X., Zhi, L., Müllen, K. Nano. Lett. 2008, 8, 323-327;<br />Feng, X.; Chandrasekhar, N.; Su, H. B.; Müllen, K., Nano. Lett. 2008, 8, 4259.;<br />Pang, S.; Tsao, H. N.; Feng, X.; Müllen, K., Adv. Mater. 2009, 31, 3488;<br />Feng, X., Marcon, V., Pisula, W., Hansen, M.R., Kirkpatrick, I., Müllen, K., Nature Mater. 2009, 8, 421;<br />Cai, J., Ruffieux, P., Jaafar, R., Bieri, M., Braun, T., Blankenburg, S., Muoth, M., Seitsonen, A. P., Saleh, M., Feng, X., Müllen, K., Fasel, R., Nature 2010, 466, 470-473;<br />Yang, S., Feng, X., Zhi, L., Cao, Q., Maier, J., Müllen, K., Adv. Mater. 2010, 22, 838; Liu, R., Wu, D., Feng, X., Müllen, K., Angew. Chem. Int. Ed. 2010, 49, 2565;<br />Käfer, D., Bashir, A., Dou, X., Witte, G., Müllen, K., Wöll, C., Adv. Mater. 2010, 22, 384;<br />Diez-Perez, I., Li, Z., Hihath, J., Li, J., Zhang, C., X., Zang, L., Dai, Y., Heng, X., Müllen, K., Tao, N. J. Nature Commun. 2010, DOI: 10.1038.</i></div>
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<i>Prof. Dr. Klaus Müllen<br />joined the Max-Planck-Society in 1989 as one of the directors of the Max-Planck Institute for Polymer Research. He obtained a Diplom-Chemiker degree at the University of Cologne in 1969 after work with Professor E. Vogel. His Ph.D. degree was granted by the University of Basel, Switzerland, in 1972 where he undertook research with Professor F. Gerson on twisted pi-systems and EPR spectroscopic properties of the corresponding radical anions. In 1972 he joined the group of Professor J.F.M. Oth at the Swiss Federal Institute of Technology in Zürich where he worked in the field of dynamic NMR spectroscopy and electrochemistry. He received his habilitation from the ETH Zürich in 1977 and was appointed Privatdozent. In 1979 he became a Professor in the Department of Organic Chemistry, University of Cologne, and accepted an offer of a chair in Organic Chemistry at the University of Mainz in 1983. He received a call to the University of Göttingen in 1988.</i></div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-25236303955547084412017-11-23T15:24:00.001+05:302017-11-23T15:24:48.291+05:30Catalytic C-H amination at its limits: challenges and solutions<div dir="ltr" style="text-align: left;" trbidi="on">
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Catalytic C-H amination at its limits: challenges and solutions</div>
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<i><b>Org. Chem. Front.</b></i>, 2017, <b>4</b>,2500-2521<br /><b>DOI</b>: 10.1039/C7QO00547D, Review Article</div>
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Damien Hazelard, Pierre-Antoine Nocquet, Philippe Compain<br />Pushing C-H amination to its limits fosters innovative synthetic solutions and offers a deeper understanding of the reaction mechanism and scope.</div>
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Catalytic C–H amination at its limits: challenges and solutions</h2>
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<span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3ADamien%20Hazelard" href="http://pubs.rsc.org/en/results?searchtext=Author%3ADamien%20Hazelard">Damien Hazelard</a>,<sup>a</sup> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3APierre-Antoine%20Nocquet" href="http://pubs.rsc.org/en/results?searchtext=Author%3APierre-Antoine%20Nocquet">Pierre-Antoine Nocquet</a><sup>a</sup> and </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3APhilippe%20Compain" href="http://pubs.rsc.org/en/results?searchtext=Author%3APhilippe%20Compain">Philippe Compain</a>*<sup>a</sup> </span></div>
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*Corresponding authors</div>
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<sup>a</sup>Laboratoire de Synthèse Organique et Molécules Bioactives (SYBIO), Université de Strasbourg/CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087 Strasbourg Cedex 2, France<br /><b>E-mail:</b> <a data-mce-href="mailto:philippe.compain@unistra.fr" href="mailto:philippe.compain@unistra.fr" title="philippe.compain@unistra.fr">philippe.compain@unistra.fr</a></div>
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Abstract</h3>
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Catalytic C–H amination reactions enable direct functionalization of non-activated C(sp<small><sup>3</sup></small>)–H bonds with high levels of regio-, chemo- and stereoselectivity. As a powerful tool to unlock the potential of inert C–H bonds, C–H amination chemistry has been applied to the preparation of synthetically challenging targets since major simplification of synthetic sequences are expected from this approach. Pushing C–H amination to its limits has led to a deeper understanding of the reaction mechanism and scope. In this review, we present a description of the specific challenges facing catalytic C–H amination in the synthesis of natural products and related compounds, as well as innovative tactics created to overcome them. By identifying and discussing the major insights gained and strategies designed, we hope that this review will stimulate further progress in C–H amination chemistry and beyond.</div>
Conclusion Since the seminal works of Du Bois in the early 2000s, the pace of discovery in the field of metal-catalysed C–H amination has been breath-taking. Not surprisingly, this synthetic tool has been applied to the total synthesis of many compounds of interest, given the high prevalence of the amino group in natural products and synthetic pharmaceuticals.67 Chemist’s confidence in the high potential of the C–H amination methodology to unlock inert C–H bonds has been demonstrated by its application to more and more challenging substrates. This has been a powerful drive for progress in the field. New valuable insights have been gained allowing, for example, a better regiochemical control via stereoelectronic and/or conformational effects. Innovative strategies have been discovered to direct the insertion event in substrates bearing a large degree of attendant functionality. Solutions have spanned from the elegant exploitation of kinetic isotope effects to the tactical use of protecting groups with different sizes or electronic characteristics. Systematic exploration of different catalytic systems has been also performed leading to the opening of new possibilities in C–H amination technology. Manganese-based catalysts have thus given rise to nitrenoids that overcome the low reactivity of primary aliphatic C–H bonds without interfering with weaker secondary/tertiary C–H bonds. Despite these impressive achievements, much remains to be done. Counterintuitive selectivity and unexplained reactivity should serve as a reminder that further studies are highly needed to understand in depth catalytic C–H amination chemistry. Many challenges remain on the way, from basic to applied research. A clear mechanistic view based on definitive evidence concerning the details of the C–N bond forming process would undoubtedly facilitate the rational design of efficient catalytic systems leading to higher regio-, chemio- and stereoselectivity. In particular, the quest for site-selective C–H amination through catalyst control has to be pursued.10d,e In this context, the development of efficient intermolecular C–H amination process still represents a major challenge and upcoming advancements are expected to increase the impact of this technology in organic synthesis. Future progress made in the field of catalytic C–H amination chemistry might also lead to industrial-scale applications in the next decade. It is likely that total synthesis of synthetically challenging targets related to natural products will continue to be a powerful driving force towards this goal.<br />
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-3480160638413129702017-11-21T19:13:00.000+05:302017-11-21T19:13:08.099+05:30Highly active, separable and recyclable bipyridine iridium catalysts for C–H borylation reactions<div dir="ltr" style="text-align: left;" trbidi="on">
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Highly active, separable and recyclable bipyridine iridium catalysts for C–H borylation reactions</h2>
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<span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AHind%20Mamlouk" href="http://pubs.rsc.org/en/results?searchtext=Author%3AHind%20Mamlouk">Hind Mamlouk</a>,<sup>a</sup> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AJakkrit%20Suriboot" href="http://pubs.rsc.org/en/results?searchtext=Author%3AJakkrit%20Suriboot">Jakkrit Suriboot</a>,<sup>b</sup> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3APraveen%20Kumar%20Manyam" href="http://pubs.rsc.org/en/results?searchtext=Author%3APraveen%20Kumar%20Manyam">Praveen Kumar Manyam</a>,<sup>a</sup> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AAhmed%20AlYazidi" href="http://pubs.rsc.org/en/results?searchtext=Author%3AAhmed%20AlYazidi">Ahmed AlYazidi</a>,<sup>a</sup> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3ADavid%20E.%20Bergbreiter" href="http://pubs.rsc.org/en/results?searchtext=Author%3ADavid%20E.%20Bergbreiter">David E. Bergbreiter</a>*<sup>b</sup> and </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3ASherzod%20T.%20Madrahimov" href="http://pubs.rsc.org/en/results?searchtext=Author%3ASherzod%20T.%20Madrahimov">Sherzod T. Madrahimov</a>*<sup>a</sup> </span></div>
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<sup>a</sup>Department of Chemistry, Texas A&M University at Qatar, P.O. Box 23874, Doha, Qatar<br /><b>E-mail:</b> <a data-mce-href="mailto:sherzod.madrahimov@qatar.tamu.edu" href="mailto:sherzod.madrahimov@qatar.tamu.edu" title="sherzod.madrahimov@qatar.tamu.edu">sherzod.madrahimov@qatar.tamu.edu</a></div>
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<sup>b</sup>Department of Chemistry, Texas A&M University, College Station, USA<br /><b>E-mail:</b> <a data-mce-href="mailto:bergbreiter@tamu.edu" href="mailto:bergbreiter@tamu.edu" title="bergbreiter@tamu.edu">bergbreiter@tamu.edu</a></div>
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Abstract</h3>
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Iridium complexes generated from Ir(<small>I</small>) precursors and PIB oligomer functionalized bpy ligands efficiently catalyzed the reactions of arenes with bis(pinacolato)diboron under mild conditions to produce a variety of arylboronate compounds. The activity of this PIB bound homogeneous catalyst is similar to that of an original non-recyclable catalyst which allows it to be used under milder conditions than other reported recyclable catalysts. This oligomer-supported Ir catalyst was successfully recovered through biphasic extraction and reused for eight cycles without a loss of activity. Biphasic separation after the initial use of the catalyst led to an insignificant amount of iridium leaching from the catalyst to the product, and no iridium leaching from the catalyst was observed in the subsequent recycling runs. Arylboronate products obtained after extraction are sufficiently pure as observed by <small><sup>1</sup></small>H and <small><sup>13</sup></small>C-NMR spectroscopy that they do not require further purification.</div>
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<img alt="Hind MAMLOUK, PhD" data-mce-src="https://media-exp2.licdn.com/media/AAEAAQAAAAAAAALlAAAAJDE3NmY5OWQzLWU5YWEtNGFlYS1hMjA3LTI3YWQ5YzJkYjhlZQ.jpg" src="https://media-exp2.licdn.com/media/AAEAAQAAAAAAAALlAAAAJDE3NmY5OWQzLWU5YWEtNGFlYS1hMjA3LTI3YWQ5YzJkYjhlZQ.jpg" style="height: auto; max-width: 100%;" /></div>
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Hind MAMLOUK, PhD</h1>
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R&D in Organic Materials Chemistry Looking for a New Challenge</div>
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3-Chloro-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anisole (5). Transparent oil. Yield: 87%.</div>
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1H NMR (600 MHz, CDCl3) δ 7.37 (s, 1H), 7.22 – 7.16 (m, 1H), 6.99 (s, 1H), 3.82 (s, 3H), 1.34 (s, 12H);</div>
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13C NMR (101 MHz, CDCl3) δ 159.88, 134.57, 126.84, 117.71, 117.43, 84.15, 55.52, 24.82.</div>
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GCMS: RT=14.55 min, M+ = 268.1 vs MW= 268.54 g.mol-1 .</div>
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Asst. Prof.</h5>
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Texas A&M University at Qatar · Chemistry</div>
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Qatar · Doha</div>
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PostDoc Position</h5>
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Northwestern University · Department of Chemistry</div>
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United States · Evanston</div>
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Graduate student</h5>
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University of Illinois, Urbana-Champaign · Department of Chemistry</div>
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United States · Urbana</div>
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Texas A&M University at Qatar</div>
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<span class="h4">David Bergbreiter</span><br />Professor<br />
<span class="h5">Contact</span><br />
<address>
Department of Chemistry<br />Texas A&M University<br />College Station, TX 77843-3255</address>
<abbr title="Phone">P:</abbr> 979-845-3437<br /><abbr title="Fax">F:</abbr> 979-845-4719<br /><a data-mce-href="mailto:#" href="mailto:#">bergbreiter@chem.tamu.edu</a><br />
<address>
<h4>
Current Activities</h4>
Our group explores new chemistry related to catalysis and polymer functionalization using the tools and precepts of synthetic organic chemistry to prepare functional oligomers or polymers that in turn are used to either effect catalysis in a greener, more environmentally benign way or to more efficiently functionalize polymers. Often this involves creatively combining the physiochemical properties of a polymer with the reactivity of a low molecular weight compound to form new materials with new functions. These green chemistry projects involve undamental research both in synthesis and catalysis but has practical aspects because of its relevance to practical problems.<br />
A common theme in our catalysis studies is exploring how soluble polymers can facilitate homogeneous catalysis. Homogeneous catalysts are ubiquitously used to prepare polymers, chemical intermediates, basic chemicals and pharmaceuticals. Such catalysts often use expensive or precious metals or expensive ligands or are used at relatively high catalyst loadings. The products often contain traces of these catalysts or ligands - traces that are undesirable for esthetic reasons or because of the potential toxicity of these impurities. Both the cost of these catalysts of these issues require catalyst/product separation - separations that often are inefficient and lead to chemical waste. These processes also use volatile organic solvents - solvents that have to be recovered and separated. Projects underway in our lab explore how soluble polymers can address each of these problems. Examples of past schemes that achieve this goal in a general way as highlighted in the Figure below.<br />
We also use functional polymers to modify existing polymers. Ongoing projects involve molecular design of additives that can more efficiently modify polymers' physical properties. We also use functional polymers in covalent layer-by-layer assembly to surface polymers' surface chemistry. An example of this work is our use of 'smart' polymers that reversibly change from being water soluble cold to being insoluble and hydrophobic on heating. Such polymers' have been used by us to prepare 'smart' catalysts, 'smart' surfaces and membranes, and to probe fundamental chemistry underlying temperature and salt-dependent protein solvation.</address>
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Dr. Praveen Kumar</h1>
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<strong>Title:</strong> Research Assistant Professor</div>
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<strong>Education:</strong> M.S., I.I.T. Roorkee<br />Ph.D., Panjab University Chandigarh (2008)<br />Visiting Fellow (w/ Prof. G. G. Balint-Kurti), Bristol University, UK<br />Postdoctoral Research Associate (w/ Prof. Svetlana Malinovskaya), Stevens Institute of Technology, Hoboken, NJ<br />Senior Postdoctoral Research Associate (w/ Prof. Seogjoo Jang), Queens College of CUNY, NY<br />
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-28861606845560725052017-11-16T18:35:00.003+05:302017-11-16T18:35:47.079+05:30Synthesis with Catalysts<div dir="ltr" style="text-align: left;" trbidi="on">
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<strong>Synthesis with Catalysts Pt. Ltd.</strong> is a company started with an aim to produce chiral and achiral precious metal based catalysts on commercial scale in line with “Clean and Green India” and “Make in India” vision of Government of India. These catalysts have been developed to promote efficient, economical and environmentally benign processes for the target compounds being produced in aroma, fine chemicals and pharmaceutical industries. These catalysts and their intermediates are also extensively used in academic and industrial R&D centres across globe. In India these catalysts are currently imported at a very prohibitive cost, due to which their use is limited for want of funds. In this direction Synthesis with Catalysts Pvt. Ltd. is striving to make these products available to indigenously available at a very competitive price at small and bulk scale. We are also doing in-house research to optimize process parameters ofvarious organic transformations particularly asymmetric hydrogenation and isomerization reactionsfor customers as and when required.<br />
For the list of our products please visit our wesite<a data-mce-href="http://www.synthesiswithcatalysts.com" href="http://www.synthesiswithcatalysts.com/">www.synthesiswithcatalysts.com</a><br />
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<ul>
<li>increase productivity,</li>
<li>develop new products with the intervention of catalysts to make the process green and clean</li>
</ul>
<ul>
<li>Highly selective catalysts for intended application</li>
<li>Competitive pricing with short delivery lead times</li>
<li>Custom product and process development</li>
</ul>
Activities:A<br />
Manufacture of Homogeneous catalysts using metal ions viz. Rh, Pt, Ir, Pd, Ru, Co, and Mn<br />
Manufacture of ligands and intermediates<br />
Pharmaceutical, bulk drugs, API, aroma chemical, essential oil industries served<br />
Focus on chiral chemistries<br />
Gram to kilogram quantities<br />
ASYMMETR<br />
<h4>
<strong>Some of the representative reactions are:</strong></h4>
<strong>ASYMMETRIC/ CHEMOSELECTIVE HYDROGENATION CATALYSTS</strong><br />
<a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-5.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-5.jpg" rel="attachment wp-att-10033"><img alt="str10" class="alignnone wp-image-10033" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-5.jpg" height="407" src="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-5.jpg" style="height: auto; max-width: 100%;" width="893" /></a><br />
<br />
Statements<br />
<ul>
<li>Catalysts are chiral metal complexes derived from a precious metal ion and chiral ligands</li>
<li>Ru used most frequently, Rh used in some cases to enhance chemo- and enantio- selectivity</li>
<li>Chiral ligands can be selected from variety of simple and substituted BINAP alone or in combination with chiral/achiral diamines</li>
<li>Suggested catalysts:<ul>
<li>RuCl<sub>2</sub>[(<em>S</em>)-BINAP](dmf)n</li>
<li>RuCl<sub>2</sub>[(<em>S</em>)- tolBINAP][(<em>S</em>,<em>S</em>)-dpen]</li>
<li>(<em>S</em>)-XylBINAP/(<em>S</em>)-DAIPEN-Ru</li>
<li>(<em>S</em>)-XylBINAP/(<em>S</em>,<em>S</em>)-DPEN-Ru</li>
<li>RuCl<sub>2</sub>[(<em>S</em>)-tolBINAP](pica)</li>
<li>RuCl[(<em>S</em>,<em>S</em>)-TsDPEN](<em>η</em><sup>6</sup>-p-cymene)</li>
<li>Ru(OTf)(TsDPEN)(<em>p</em>-cymene)</li>
<li>BINAP-Ru(II) dicarboxylate complexes</li>
</ul>
</li>
</ul>
<h4>
<strong>ENANTIOSELECTIVE EPOXIDATION / HKR / DKR</strong></h4>
<a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-4.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-4.jpg" rel="attachment wp-att-10032"><img alt="str10" class="alignnone wp-image-10032" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-4.jpg" height="511" src="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-4.jpg" style="height: auto; max-width: 100%;" width="917" /></a><br />
<br />
Statements:<br />
<ul>
<li>Transition metal complexes are used for chiral and non-chiral epoxidation of internal and prochiral olefins</li>
<li>The epoxides are important intermediates for host of industrially important products</li>
<li>In cases where epoxides are required in high optical purity, racemic epoxides can be subjected to Hydrolytic kinetic resolution (HKR), Aminolytic kinetic resolution (AKR), Dynamic kinetic resolutions (DKR)</li>
<li>Suggested catalysts:<ul>
<li>Mn, Co, Cr, Al complexes of chiral SALEN ligands</li>
</ul>
</li>
</ul>
<strong>ASYMMETRIC ISOMERIZATION</strong><br />
<br />
<a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-3.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-3.jpg" rel="attachment wp-att-10031"><img alt="str10" class="alignnone wp-image-10031" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-3.jpg" height="283" src="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-3.jpg" style="height: auto; max-width: 100%;" width="666" /></a><br />
Double bond migration reactions<br />
<a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-2.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-2.jpg" rel="attachment wp-att-10030"><img alt="str10" class="alignnone wp-image-10030" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-2.jpg" height="437" src="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-2.jpg" style="height: auto; max-width: 100%;" width="719" /></a><br />
Statements:<br />
<ul>
<li>Rh-catalyzed asymmetric isomerization of allylic amines into the corresponding enamines is one of the most revered industrial organic transformation in asymmetric catalysis</li>
<li>It has accommodated a wide range of substrates and is a key step in the industrial production of menthol</li>
<li>Other industrially important isomerization is migration of terminal double bond to produce selectively trans-internal olefins</li>
<li>Commercially important products like isoeugenol and trans-anetheole are produced by these transformations</li>
<li>Suggested catalysts:<ul>
<li>Ru(acac)<sub>3</sub></li>
<li>RuHCl(CO)(PPh<sub>3</sub>)<sub>3</sub></li>
<li>Rh/Pd complexes</li>
</ul>
</li>
</ul>
Tree of popular asymmetric organic transformations<br />
<br />
<a data-mce-href="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-1.jpg" href="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-1.jpg" rel="attachment wp-att-10029"><img alt="str10" class="alignnone wp-image-10029" data-mce-src="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-1.jpg" height="821" src="http://www.allfordrugs.com/wp-content/uploads/2017/11/str10-1.jpg" style="height: auto; max-width: 100%;" width="881" /></a></div>
</div>
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<span class="ember-view" id="ember6177">At Chiral India event in Mumbai where our technical director Dr. Abdi Is a speaker. With </span><a class="feed-link feed-base-main-content__mention ember-view" data-control-name="mention" data-mce-href="https://www.linkedin.com/in/basuagarwal/" data-mce-tabindex="0" href="https://www.linkedin.com/in/basuagarwal/" id="ember6180"><span data-entity-hovercard-id="urn:li:fs_miniProfile:ACoAAAEmsX0BroF7ZS47p3Zldsz4kEZT_AUYMBE">Basu Agarwal</span></a><span class="ember-view" id="ember6182"></span></div>
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Basu Agarwal</h1>
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CEO at Synthesis with Catalysts Pvt Ltd</div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-13573292200620396302017-11-05T17:50:00.003+05:302017-11-05T17:59:17.627+05:30Oxidant- and hydrogen acceptor-free palladium catalyzed dehydrogenative cyclization of acylhydrazones to substituted oxadiazoles<div dir="ltr" style="text-align: left;" trbidi="on">
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<a href="http://pubs.rsc.org/en/Content/ArticleLanding/2018/QO/C7QO00749C" style="color: #000099;">Oxidant- and hydrogen acceptor-free palladium catalyzed dehydrogenative cyclization of acylhydrazones to substituted oxadiazoles</a></h4>
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<i><b>Org. Chem. Front.</b></i>, 2018, Advance Article<br />
<b>DOI</b>: 10.1039/C7QO00749C, Research Article</div>
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<div style="font-family: helvetica, arial, sans-serif; font-size: 14px;">
Qiangqiang Jiang, Xinghui Qi, Chenyang Zhang, Xuan Ji, Jin Li, Renhua Liu</div>
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An efficient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles has been developed through palladium(0) catalyzed dehydrogenative cyclization of <em>N</em>-arylidenearoylhydrazides without oxidants and hydrogen acceptors.</div>
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Oxidant- and hydrogen acceptor-free palladium catalyzed dehydrogenative cyclization of acylhydrazones to substituted oxadiazoles</h2>
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<span class="article__author-link" style="line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AQiangqiang%20Jiang" style="color: #2d7ea9;">Qiangqiang Jiang</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span> </span><span class="article__author-link" style="line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AXinghui%20Qi" style="color: #2d7ea9;">Xinghui Qi</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span> </span><span class="article__author-link" style="line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AChenyang%20Zhang" style="color: #2d7ea9;">Chenyang Zhang</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span> </span><span class="article__author-link" style="line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AXuan%20Ji" style="color: #2d7ea9;">Xuan Ji</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span> </span><span class="article__author-link" style="line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AJin%20Li" style="color: #2d7ea9;">Jin Li</a><span style="font-size: 16px;">*</span><span style="position: relative; top: -0.4em; vertical-align: baseline;">b</span> and </span><span class="article__author-link" style="line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3ARenhua%20Liu" style="color: #2d7ea9;">Renhua Liu</a><span style="font-size: 16px;">*</span><span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span> </span></div>
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<span style="display: table-cell; padding-left: 4px; width: 7px;">*</span><span style="display: table-cell; padding-left: 12px;">Corresponding authors</span></div>
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<span style="display: table-cell; padding-left: 4px; width: 7px;"><span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span></span><span style="display: table-cell; padding-left: 12px;">School of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, China<br /><b>E-mail:</b> <a href="mailto:liurh@ecust.edu.cn" style="color: #9d3d99;" title="liurh@ecust.edu.cn">liurh@ecust.edu.cn</a></span></div>
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<span style="display: table-cell; padding-left: 4px; width: 8px;"><span style="position: relative; top: -0.4em; vertical-align: baseline;">b</span></span><span style="display: table-cell; padding-left: 12px;">China Catalyst Holding Co., Ltd, Jingjiu Road 3, Chemical Park, Songmu Island, Puwan New District, Dalian 116699, China<br /><b>E-mail:</b> <a href="mailto:lijin@china-catalyst.com" style="color: #9d3d99;" title="lijin@china-catalyst.com">lijin@china-catalyst.com</a></span></div>
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Abstract</h3>
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An efficient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles has been developed through palladium(0) catalyzed dehydrogenative cyclization of <em>N</em>-arylidenearoylhydrazides. By using this method, a wide range of functionalized and potentially biologically relevant 1,3,4-oxadiazole-containing compounds have been accessed in moderate to high isolated yields. The dehydrogenative cyclization process is characterized by the nonuse of any sacrificing hydrogen acceptors or oxidants and hydrogen gas as the only by-product, and therefore circumvents the recurring problems of over-oxidation and the compatibility with easily oxidizable functionalities in oxidation protocols.</div>
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109.6 mg, 87 % yield; White solid,<br />
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1H NMR (400 MHz, CDCl3) δ 8.13 – 8.08 (m, 2H), 8.06 (d, J = 8.7 Hz,
2H), 7.52 (m, 3H), 7.01 (d, J = 8.7 Hz, 2H), 3.86 (s, 3H);<br />
<br />
13C NMR (100 MHz, CDCl3) δ 164.51, 164.10, 162.33,
131.54, 129.03, 128.67, 126.80, 124.05, 116.38, 114.50, 55.46; M.p. 145-146 oC.</div>
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2-(4-methoxyphenyl)-5-phenyl-1,3,4-oxadiazole</div>
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1H NMR CDCL3</div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-41147075091213479742017-11-05T09:13:00.003+05:302017-11-05T14:14:39.646+05:30Learn spectroscopy, Valeric acid or pentanoic acid. PROBLEM 1<div dir="ltr" style="text-align: left;" trbidi="on">
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<img alt="Image result for MOTHER TO TEACH NMR" src="https://m1.behance.net/rendition/modules/142826947/disp/d6ae3b784ab6fd0fb163d9466712176b.gif" /><br />
HE IS EXCITED TOO<br />
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<tr><td align="left" colspan="2" style="font-stretch: normal; line-height: 19.5px; padding-left: 28px; word-break: break-all; word-wrap: break-word;"><b>Product Name:</b> <span id="ContentPlaceHolder1_ProdName1"><a href="https://www.chemicalbook.com/ProductChemicalPropertiesCB2309387_EN.htm" style="color: #003399; outline: none;">Valeric acid</a></span></td></tr>
<tr><td align="left" colspan="2" style="font-stretch: normal; line-height: 19.5px; padding-left: 28px; word-break: break-all; word-wrap: break-word;"><b>CAS:</b><span id="ContentPlaceHolder1_CAS1"><a href="https://www.chemicalbook.com/CASEN_109-52-4.htm" id="A1" name="top" style="color: #003399; outline: none;">109-52-4</a></span><br />
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<span style="background-color: white; color: #616161; font-family: "arial"; font-size: 15px;">valeric acid</span><br />
<span style="background-color: white; color: #616161; font-family: "arial"; font-size: 15px;">pentansäure</span><br />
<span style="background-color: white; color: #616161; font-family: "arial"; font-size: 15px;">acide pentanoic</span><br />
<span style="background-color: white; color: #616161; font-family: "arial"; font-size: 15px;">ペンタン酸</span><br />
<span style="background-color: white; color: #616161; font-family: "arial"; font-size: 15px;">109-52-4 CAS</span><br />
<span style="background-color: white; color: #616161; font-family: "arial" , "tahoma" , "helvetica" , "freesans" , sans-serif;">C5H10O2</span><br />
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<img id="ContentPlaceHolder1_SpectrumImgURL" src="https://www.chemicalbook.com/Spectrum/109-52-4_MS.gif" style="border: none; outline: none; width: 630px;" /></div>
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<span style="background-color: #cccccc; font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">Valeric acid, or pentanoic acid.</span><br />
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<span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">This <sup>13</sup>C spectrum exhibits </span><span style="font-family: "arial" , "helvetica" , sans-serif; font-size: x-large;"></span><span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">resonances at the following chemical shifts, and with the multiplicities indicated:</span></div>
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<tr><td><b><span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">Shift (ppm)</span></b></td><td><div align="center">
<b><span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">Mult.</span></b></div>
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<tr><td><span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">180.8</span></td><td><div align="center">
<span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">S</span></div>
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<tr><td><span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">33.8</span></td><td><div align="center">
<span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">T</span></div>
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<tr><td><span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">26.8</span></td><td><div align="center">
<span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">T</span></div>
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<tr><td><span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">22.4</span></td><td><div align="center">
<span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">T</span></div>
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<tr><td><span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">3.58</span></td><td><div align="center">
<span style="font-family: "arial" , "helvetica" , sans-serif; font-size: medium;">Q</span></div>
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<span style="background-color: #85afd7; font-family: "arial" , "helvetica" , sans-serif; font-size: x-large; text-align: -webkit-center;"><b> (</b></span><b style="background-color: #85afd7; text-align: -webkit-center;"><span style="font-family: "arial" , "helvetica" , sans-serif; font-size: x-large;">C<sub>5</sub>H<sub>10</sub>O<sub>2</sub>)</span></b></div>
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A= 13.4</div>
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B=22.4</div>
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C=26.8</div>
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D=33.8</div>
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E=180.6</div>
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1H NMR BELOW</div>
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t=0.78</div>
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m=1.22</div>
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m=1.46</div>
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t=2.2</div>
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s=11.8</div>
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NMR IS EASY</div>
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EVEN MOM CAN TEACH YOU</div>
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<img alt="2D [1H,1H]-TOCSY, 7.4 spectrum for Valeric acid" src="http://www.bmrb.wisc.edu/ftp/pub/bmrb/metabolomics/entry_directories/bmse000345/nmr/set01/spectra/HH_TOCSY.png" height="494" width="640" /></div>
<h3 style="font-family: Arial, Verdana, Helvetica, sans-serif;">
2D [1H,1H]-TOCSY</h3>
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<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">Concentration:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 100 mM</span></div>
<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">temperature:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 298 K</span><br />
<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">pH:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 7.4</span><br />
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<img alt="1D DEPT90, 7.4 spectrum for Valeric acid" src="http://www.bmrb.wisc.edu/ftp/pub/bmrb/metabolomics/entry_directories/bmse000345/nmr/set01/spectra/DEPT_90.png" height="453" width="640" /></div>
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1D DEPT90</h3>
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<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">Concentration:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 100 mM</span></div>
<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">temperature:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 298 K</span><br />
<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">pH:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 7.4</span><br />
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<img alt="1D DEPT135, 7.4 spectrum for Valeric acid" src="http://www.bmrb.wisc.edu/ftp/pub/bmrb/metabolomics/entry_directories/bmse000345/nmr/set01/spectra/DEPT_135.png" height="453" width="640" /></div>
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1D DEPT135</h3>
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<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">Concentration:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 100 mM</span></div>
<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">temperature:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 298 K</span><br />
<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">pH:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 7.4</span><br />
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<img alt="2D [1H,13C]-HSQC, 7.4 spectrum for Valeric acid" src="http://www.bmrb.wisc.edu/ftp/pub/bmrb/metabolomics/entry_directories/bmse000345/nmr/set01/spectra/1H_13C_HSQC.png" /></div>
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2D [1H,13C]-HSQC</h3>
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<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">Concentration:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 100 mM</span></div>
<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">temperature:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 298 K</span><br />
<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">pH:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 7.4</span><br />
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<img alt="2D [1H,13C]-HMBC, 7.4 spectrum for Valeric acid" src="http://www.bmrb.wisc.edu/ftp/pub/bmrb/metabolomics/entry_directories/bmse000345/nmr/set01/spectra/1H_13C_HMBC.png" height="494" width="640" /></div>
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2D [1H,13C]-HMBC</h3>
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<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">Concentration:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 100 mM</span></div>
<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">temperature:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 298 K</span><br />
<b style="font-family: Arial, Verdana, Helvetica, sans-serif; font-size: 16px; text-align: start;">pH:</b><span style="font-family: "arial" , "verdana" , "helvetica" , sans-serif; font-size: 16px;"> 7.4</span><br />
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<span style="background-color: white; color: red; font-family: Arial, Helvetica, sans-serif; font-size: 13.92px; text-align: start;">“ORG SYNTHESIS INT” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent</span></div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-83466425658642663582017-10-20T09:03:00.001+05:302017-10-20T09:03:50.179+05:30PHTHALAN<div dir="ltr" style="text-align: left;" trbidi="on">
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<a href="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEjoa0tMxANKTrECATa3cGhXXSAvOkvaQhm2CaSKsRwOIc-JmJpZ8t9z11z_3RziAP-PgxVRjNuzyLqF-hiSlb50f450cKDlEi0UPcUquO5-IsRz_8zGDeR2IObM1Am3HqocDF05O_5NFge7/s1600/STR7.JPG" imageanchor="1" style="margin-left: 1em; margin-right: 1em;"><img border="0" data-original-height="484" data-original-width="661" height="468" src="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEjoa0tMxANKTrECATa3cGhXXSAvOkvaQhm2CaSKsRwOIc-JmJpZ8t9z11z_3RziAP-PgxVRjNuzyLqF-hiSlb50f450cKDlEi0UPcUquO5-IsRz_8zGDeR2IObM1Am3HqocDF05O_5NFge7/s640/STR7.JPG" width="640" /></a></div>
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Phtalan<br />
<h1 class="summary-title extra-short is-capitalized" style="background-color: white; box-sizing: border-box; clear: left; color: #212121; font-size: 4em; font-weight: 400; line-height: normal; margin: 0px; min-width: 50%; text-transform: capitalize;">
<span style="box-sizing: border-box;">PHTHALAN</span></h1>
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<ol class="multicolumn" start="1" style="background-color: white; box-sizing: border-box; color: #212121; font-size: 15px; margin: 0px; min-width: 10em; padding: 0px 1em 1.5em 2em; white-space: nowrap;"><span style="box-sizing: border-box;">
<li style="box-sizing: border-box; margin: 0px; padding: 0.2em 0px;"><a href="https://www.ncbi.nlm.nih.gov/pcsubstance/?term=%22PHTHALAN%22%5BCompleteSynonym%5D%20AND%2010327%5BStandardizedCID%5D" rel="nofollow" style="background: transparent; box-sizing: border-box; color: #006699; outline-width: 0px;">PHTHALAN</a></li>
<li style="box-sizing: border-box; margin: 0px; padding: 0.2em 0px;"><a href="https://www.ncbi.nlm.nih.gov/pcsubstance/?term=%221%2C3-Dihydroisobenzofuran%22%5BCompleteSynonym%5D%20AND%2010327%5BStandardizedCID%5D" rel="nofollow" style="background: transparent; box-sizing: border-box; color: #006699; outline: 0px;">1,3-Dihydroisobenzofuran</a></li>
<li style="box-sizing: border-box; margin: 0px; padding: 0.2em 0px;"><a href="https://www.ncbi.nlm.nih.gov/pcsubstance/?term=%22496-14-0%22%5BCompleteSynonym%5D%20AND%2010327%5BStandardizedCID%5D" rel="nofollow" style="background: transparent; box-sizing: border-box; color: #006699; outline-width: 0px;">496-14-0</a></li>
<li style="box-sizing: border-box; margin: 0px; padding: 0.2em 0px;"><a href="https://www.ncbi.nlm.nih.gov/pcsubstance/?term=%22Isocoumaran%22%5BCompleteSynonym%5D%20AND%2010327%5BStandardizedCID%5D" rel="nofollow" style="background: transparent; box-sizing: border-box; color: #006699; outline-width: 0px;">Isocoumaran</a></li>
<li style="box-sizing: border-box; margin: 0px; padding: 0.2em 0px;"><a href="https://www.ncbi.nlm.nih.gov/pcsubstance/?term=%221%2C3-Dihydro-2-benzofuran%22%5BCompleteSynonym%5D%20AND%2010327%5BStandardizedCID%5D" rel="nofollow" style="background: transparent; box-sizing: border-box; color: #006699; outline-width: 0px;">1,3-Dihydro-2-benzofuran</a></li>
<li style="box-sizing: border-box; margin: 0px; padding: 0.2em 0px;"><a href="https://www.ncbi.nlm.nih.gov/pcsubstance/?term=%22Isobenzofuran%2C%201%2C3-dihydro-%22%5BCompleteSynonym%5D%20AND%2010327%5BStandardizedCID%5D" rel="nofollow" style="background: transparent; box-sizing: border-box; color: #006699; outline-width: 0px;">Isobenzofuran, 1,3-dihydro-</a></li>
<li style="box-sizing: border-box; margin: 0px; padding: 0.2em 0px;"><a href="https://www.ncbi.nlm.nih.gov/pcsubstance/?term=%22o-Xylylene%20oxide%22%5BCompleteSynonym%5D%20AND%2010327%5BStandardizedCID%5D" rel="nofollow" style="background: transparent; box-sizing: border-box; color: #006699; outline-width: 0px;">o-Xylylene oxide</a></li>
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<span style="box-sizing: border-box;"><img alt="PHTHALAN.png" src="https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?cid=10327&t=l" /></span><br />
<span style="box-sizing: border-box;">1H NMR PREDICT</span></div>
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<a href="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEi8AI6heFUUktum5bmj5D2T7D_my__FU4DKrw1OpDVXreRQTYSMMPSoj8bCcytSYlr8rq_P84awoqif4NJH8fgtUAwjDCkfyaI_QteIIV7QrShwhvgRB5AwLfui3LgI_mna7O6y5wLr3lzX/s1600/STR7.JPG" imageanchor="1" style="margin-left: 1em; margin-right: 1em;"><img border="0" data-original-height="257" data-original-width="472" height="348" src="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEi8AI6heFUUktum5bmj5D2T7D_my__FU4DKrw1OpDVXreRQTYSMMPSoj8bCcytSYlr8rq_P84awoqif4NJH8fgtUAwjDCkfyaI_QteIIV7QrShwhvgRB5AwLfui3LgI_mna7O6y5wLr3lzX/s640/STR7.JPG" width="640" /></a></div>
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<b style="background-color: white; font-family: sans-serif; font-size: 12.7px;"><br /></b><b style="background-color: white; font-family: sans-serif; font-size: 12.7px;">13C NMR PREDICT</b><br />
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<a href="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEiVxhonkMNQH03ViYZX1kOjqf77v7Dthlhs5dTKDbghzlwdAG0K1c8U29CNYFeSrD4sdScpb4lqXCKBJBdYmeh5SzoVgo8AflDFtCSXohf1fmiO_MFSd4hBhHap0wbRA9RoXX_sVI6tPc1m/s1600/STR7.JPG" imageanchor="1" style="margin-left: 1em; margin-right: 1em;"><img border="0" data-original-height="145" data-original-width="269" height="344" src="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEiVxhonkMNQH03ViYZX1kOjqf77v7Dthlhs5dTKDbghzlwdAG0K1c8U29CNYFeSrD4sdScpb4lqXCKBJBdYmeh5SzoVgo8AflDFtCSXohf1fmiO_MFSd4hBhHap0wbRA9RoXX_sVI6tPc1m/s640/STR7.JPG" width="640" /></a></div>
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<a href="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEgXbf1pq4Jj-zd4b4barAGc2lOSgKDy8YIOxZJz33VVqtNXlKHv9HCn7a-4NoXiaA6zzHeITmC9m7mZ6DyOFOOW9fsgan_sAKygW7oBuBgIrAr6vL88GFcDvHd1JAtlhT1E3DdNxotzGMnO/s1600/STR8.JPG" imageanchor="1" style="margin-left: 1em; margin-right: 1em;"><img border="0" data-original-height="293" data-original-width="655" height="286" src="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEgXbf1pq4Jj-zd4b4barAGc2lOSgKDy8YIOxZJz33VVqtNXlKHv9HCn7a-4NoXiaA6zzHeITmC9m7mZ6DyOFOOW9fsgan_sAKygW7oBuBgIrAr6vL88GFcDvHd1JAtlhT1E3DdNxotzGMnO/s640/STR8.JPG" width="640" /></a></div>
<b style="background-color: white; font-family: sans-serif; font-size: 12.7px;"><br /></b><b style="background-color: white; font-family: sans-serif; font-size: 12.7px;"><br /></b><b style="background-color: white; font-family: sans-serif; font-size: 12.7px;"><br /></b><b style="background-color: white; font-family: sans-serif; font-size: 12.7px;"><br /></b><b style="background-color: white; font-family: sans-serif; font-size: 12.7px;"><br /></b><b style="background-color: white; font-family: sans-serif; font-size: 12.7px;">Phthalane</b><span style="background-color: white; font-family: sans-serif; font-size: 12.7px;"> is a bicyclic aromatic organic compound. It is also known as isocoumaran, or 1,3-dihydro-2-benzofuran. Derivatives are found in the drug </span><a href="https://en.wikipedia.org/wiki/Citalopram" style="background: none rgb(255, 255, 255); color: #5a3696; font-family: sans-serif; font-size: 12.7px;" title="Citalopram">Citalopram</a><span style="background-color: white; font-family: sans-serif; font-size: 12.7px;">, and drug candidate </span><a class="new" href="https://en.wikipedia.org/w/index.php?title=Lu_10-171&action=edit&redlink=1" style="background: none rgb(255, 255, 255); color: #a55858; font-family: sans-serif; font-size: 12.7px;" title="Lu 10-171 (page does not exist)">Lu 10-171</a><span style="background-color: white; font-family: sans-serif; font-size: 12.7px;">. It can be oxidised to </span><a href="https://en.wikipedia.org/wiki/Phthalic_acid" style="background: none rgb(255, 255, 255); color: #5a3696; font-family: sans-serif; font-size: 12.7px;" title="Phthalic acid">phthalic acid</a><span style="background-color: white; font-family: sans-serif; font-size: 12.7px;">.</span><br />
<table class="infobox bordered" style="background-color: #f8f9fa; border-collapse: collapse; border-spacing: 3px; border: 1px solid rgb(162, 169, 177); clear: right; color: black; font-family: sans-serif; font-size: 11.176px; line-height: 1.5em; margin: 0.5em 0px 0.5em 1em; padding: 0.2em; width: 22em;"><caption style="font-size: 13.97px; font-weight: bold; padding: 0.2em;">Phthalane</caption><tbody>
<tr><td colspan="2" style="border: 1px solid rgb(162, 169, 177); padding: 2px; text-align: center; vertical-align: top;"><a class="image" href="https://en.wikipedia.org/wiki/File:Phthalan-2D-skeletal.png" style="background: none; color: #5a3696;"><img alt="Phthalan-2D-skeletal.png" data-file-height="685" data-file-width="1100" height="125" src="https://upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Phthalan-2D-skeletal.png/200px-Phthalan-2D-skeletal.png" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Phthalan-2D-skeletal.png/300px-Phthalan-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Phthalan-2D-skeletal.png/400px-Phthalan-2D-skeletal.png 2x" style="border: 0px; vertical-align: middle;" width="200" /></a></td></tr>
<tr><th colspan="2" style="background: rgb(248, 234, 186); border: 1px solid rgb(162, 169, 177); text-align: center; vertical-align: top;">Names</th></tr>
<tr><td colspan="2" style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><a href="https://en.wikipedia.org/wiki/Chemical_nomenclature" style="background: none; color: #5a3696;" title="Chemical nomenclature">IUPAC name</a><br />
<div style="max-width: 22em; padding-left: 1.7em; word-wrap: break-word;">
1,3-dihydroisobenzofuran</div>
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<tr><th colspan="2" style="background: rgb(248, 234, 186); border: 1px solid rgb(162, 169, 177); text-align: center; vertical-align: top;">Identifiers</th></tr>
<tr><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><div style="line-height: 1.2em; padding: 0.1em 0px;">
<a href="https://en.wikipedia.org/wiki/CAS_Registry_Number" style="background: none; color: #5a3696;" title="CAS Registry Number">CAS Number</a></div>
</td><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><div class="plainlist">
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<li style="margin-bottom: 0px;"><span title="www.commonchemistry.org"><a class="external text" href="http://www.commonchemistry.org/ChemicalDetail.aspx?ref=496-14-0" rel="nofollow" style="background: linear-gradient(transparent, transparent) right center no-repeat, url("about:blank"); color: #bb6633; padding-right: 15px;">496-14-0</a></span><sup style="font-size: 8.9408px; line-height: 1;"> <img alt="Yes" data-file-height="600" data-file-width="600" height="7" src="https://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" style="border: 0px; vertical-align: middle;" width="7" /></sup></li>
</ul>
</div>
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<tr><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><div style="line-height: 1.2em; padding: 0.1em 0px;">
3D model (<a class="mw-redirect" href="https://en.wikipedia.org/wiki/JSmol" style="background: none; color: #5a3696;" title="JSmol">JSmol</a>)</div>
</td><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><div class="plainlist">
<ul style="line-height: inherit; list-style: none none; margin: 0px; padding: 0px;">
<li style="margin-bottom: 0px;"><span title="chemapps.stolaf.edu (3D interactive model)"><a class="external text" href="http://chemapps.stolaf.edu/jmol/jmol.php?model=c2ccc1COCc1c2" rel="nofollow" style="background: linear-gradient(transparent, transparent) right center no-repeat, url("about:blank"); color: #663366; padding-right: 15px;">Interactive image</a></span></li>
</ul>
</div>
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<tr><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><a href="https://en.wikipedia.org/wiki/ChemSpider" style="background: none; color: #5a3696;" title="ChemSpider">ChemSpider</a></td><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><div class="plainlist">
<ul style="line-height: inherit; list-style: none none; margin: 0px; padding: 0px;">
<li style="margin-bottom: 0px;"><span title="www.chemspider.com"><a class="external text" href="http://www.chemspider.com/Chemical-Structure.9904.html" rel="nofollow" style="background: linear-gradient(transparent, transparent) right center no-repeat, url("about:blank"); color: #663366; padding-right: 15px;">9904</a></span><sup style="font-size: 8.9408px; line-height: 1;"> <img alt="" data-file-height="600" data-file-width="525" height="8" src="https://upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" style="border: 0px; vertical-align: middle;" width="7" /></sup></li>
</ul>
</div>
</td></tr>
<tr><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><a class="mw-redirect" href="https://en.wikipedia.org/wiki/ECHA_InfoCard" style="background: none; color: #5a3696;" title="ECHA InfoCard">ECHA InfoCard</a></td><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><a class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.007.106" rel="nofollow" style="background: linear-gradient(transparent, transparent) right center no-repeat, url("about:blank"); color: #663366; padding-right: 15px;">100.007.106</a></td></tr>
<tr><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><a href="https://en.wikipedia.org/wiki/European_Community_number" style="background: none; color: #5a3696;" title="European Community number">EC Number</a></td><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;">207-815-2</td></tr>
<tr><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><div style="line-height: 1.2em; padding: 0.1em 0px;">
<a href="https://en.wikipedia.org/wiki/PubChem" style="background: none; color: #5a3696;" title="PubChem">PubChem</a> <abbr style="border-bottom: 0px; cursor: help;" title="Compound ID">CID</abbr></div>
</td><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><div class="plainlist">
<ul style="line-height: inherit; list-style: none none; margin: 0px; padding: 0px;">
<li style="margin-bottom: 0px;"><span title="pubchem.ncbi.nlm.nih.gov"><a class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/10327" rel="nofollow" style="background: linear-gradient(transparent, transparent) right center no-repeat, url("about:blank"); color: #663366; padding-right: 15px;">10327</a></span></li>
</ul>
</div>
</td></tr>
<tr><td colspan="2" style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><div class="NavFrame collapsed" id="NavFrame1" style="border-collapse: collapse; border: none; font-size: 10.6172px; margin: 0px; padding: 0px; text-align: center;">
<div class="NavHead" style="background: transparent; font-size: 11.1481px; line-height: 1.6em; position: relative; text-align: left;">
<a href="https://en.wikipedia.org/wiki/International_Chemical_Identifier" style="background: none; color: #5a3696;" title="International Chemical Identifier">InChI</a><a class="NavToggle" href="https://en.wikipedia.org/wiki/Phthalane#" id="NavToggle1" style="background: none; color: #5a3696; font-size: 10.0333px; position: absolute; right: 3px; top: 0px;">[show]</a></div>
</div>
</td></tr>
<tr><td colspan="2" style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><div class="NavFrame collapsed" id="NavFrame2" style="border-collapse: collapse; border: none; font-size: 10.6172px; margin: 0px; padding: 0px; text-align: center;">
<div class="NavHead" style="background: transparent; font-size: 11.1481px; line-height: 1.6em; position: relative; text-align: left;">
<a href="https://en.wikipedia.org/wiki/Simplified_molecular-input_line-entry_system" style="background: none; color: #5a3696;" title="Simplified molecular-input line-entry system">SMILES</a><a class="NavToggle" href="https://en.wikipedia.org/wiki/Phthalane#" id="NavToggle2" style="background: none; color: #5a3696; font-size: 10.0333px; position: absolute; right: 3px; top: 0px;">[show]</a></div>
</div>
</td></tr>
<tr><th colspan="2" style="background: rgb(248, 234, 186); border: 1px solid rgb(162, 169, 177); text-align: center; vertical-align: top;">Properties</th></tr>
<tr><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><div style="line-height: 1.2em; padding: 0.1em 0px;">
<a href="https://en.wikipedia.org/wiki/Chemical_formula" style="background: none; color: #5a3696;" title="Chemical formula">Chemical formula</a></div>
</td><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;">C<sub style="font-size: 8.9408px; line-height: 1;">8</sub>H<sub style="font-size: 8.9408px; line-height: 1;">8</sub>O</td></tr>
<tr><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;"><a href="https://en.wikipedia.org/wiki/Molar_mass" style="background: none; color: #5a3696;" title="Molar mass">Molar mass</a></td><td style="border: 1px solid rgb(162, 169, 177); vertical-align: top;">120.148</td></tr>
<tr><td colspan="2" style="background: rgb(248, 234, 186); border: 1px solid rgb(162, 169, 177); vertical-align: top;"><div style="margin: 0px auto;">
<div style="line-height: 1.2em; padding: 0.1em 0px;">
Except where otherwise noted, data are given for materials in their <a href="https://en.wikipedia.org/wiki/Standard_state" style="background: none; color: #5a3696;" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div>
</div>
</td></tr>
</tbody></table>
<br />
<br />
<a href="http://www.rsc.org/suppdata/gc/c4/c4gc01822b/c4gc01822b1.pdf">////////</a>////////</div>
DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-29143403102197912572017-10-16T18:39:00.000+05:302017-10-16T18:39:09.370+05:30Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis<div dir="ltr" style="text-align: left;" trbidi="on">
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<h1 style="background-color: white; border: 0px; color: #333333; font-family: Arial, Helvetica, sans-serif; font-size: 27.84px; font-weight: normal; line-height: 1.1em; margin: 0.5em 0px; outline: 0px; padding: 0px;">
<span style="border: 0px; color: maroon; font-size: 27.84px; margin: 0px; outline: 0px; padding: 0px;">Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis</span></h1>
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<span style="border: 0px; color: red; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">How to cite this article:</span><br /><span style="border: 0px; color: red; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Fanelli, F.; Parisi, G.; Degennaro, L.; Luisi, R. <i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Beilstein J. Org. Chem.</i> <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">2017,</b> <i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">13,</i> 520–542. <a href="https://doi.org/10.3762%2Fbjoc.13.51" style="border: 0px; color: red; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;" target="_blank">doi:10.3762/bjoc.13.51</a></span></div>
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<li style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><a data-original-title="" data-placement="bottom" data-popover-content="#author1" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title="">Flavio</a> <a data-original-title="" data-placement="bottom" data-popover-content="#author1" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title="">Fanelli</a>,</li>
<li style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><a data-original-title="" data-placement="bottom" data-popover-content="#author2" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title="">Giovanna</a> <a data-original-title="" data-placement="bottom" data-popover-content="#author2" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title="">Parisi</a>,</li>
<li style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><a data-original-title="" data-placement="bottom" data-popover-content="#author3" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title="">Leonardo</a> <a data-original-title="" data-placement="bottom" data-popover-content="#author3" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title="">Degennaro</a> and</li>
<li style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><a data-original-title="" data-placement="bottom" data-popover-content="#author4" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title="">Renzo</a> <a data-original-title="" data-placement="bottom" data-popover-content="#author4" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title="">Luisi</a></li>
</ol>
</div>
<div class="panel-body" style="background-color: white; border: 0px; font-family: Arial, Helvetica, sans-serif; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">
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<div class="margin-bottom__none" style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
Department of Pharmacy – Drug Sciences, University of Bari “A. Moro”, FLAME-Lab – Flow Chemistry and Microreactor Technology Laboratory, Via E. Orabona 4, 70125, Bari. Italy</div>
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<li style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"> Corresponding author email</li>
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<a href="https://www.beilstein-journals.org/bjoc/series/63" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">This article is part of the Thematic Series “Green chemistry”.</a></div>
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Guest Editor: L. Vaccaro<br /><i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Beilstein J. Org. Chem.</i> <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">2017,</b> <i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">13,</i> 520–542. doi:10.3762/bjoc.13.51<br /><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Received </strong>14 Nov 2016, <strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Accepted </strong>20 Feb 2017, <strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Published </strong>14 Mar 2017</div>
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Abstract</h2>
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Microreactor technology and flow chemistry could play an important role in the development of green and sustainable synthetic processes. In this review, some recent relevant examples in the field of flash chemistry, catalysis, hazardous chemistry and continuous flow processing are described. Selected examples highlight the role that flow chemistry could play in the near future for a sustainable development.</div>
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<strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Keywords: </strong>flash chemistry; flow chemistry; green chemistry; microreactor technology; sustainable synthesis</div>
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Introduction</h2>
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Green chemistry’s birth was driven by the necessity to consider and face the urgent question of sustainability. Chemical production concerns an extended range of fields such as textiles, construction, food, cosmetic components, pharmaceuticals and so forth. An innovative approach to the chemistry world requires new strategies and criteria for an intelligent chemistry. It is understood that all this matter has big implications in economy and politics. Recent studies predicted a growth of green chemical processing up to $100 billion in 2020 (Pike Research study) <a data-original-title="" data-placement="bottom" data-popover-content="#link1-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link1" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[1]. All this offers important and arduous challenges expressed in terms of new synthetic strategies using sustainable, safe, and less toxic materials. On green chemistry we can read Paul Anastas and John Warne’s 12 principles, set up in 1998, which illustrate the characteristics of a greener chemical process or product <a data-original-title="" data-placement="bottom" data-popover-content="#link2-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link2" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[2]. Microreactor technology and flow chemistry could play a pivotal role in the context of sustainable development. In fact, flow chemistry is becoming a new technique for fulfilling several of the twelve green chemistry principles. The microreactor approach, could provide protection, preserves atom economy, guarantees less hazardous chemical synthesis and allows the use of safer solvents and auxiliaries. Furthermore, it pushes towards designing of chemistry with a lower environmental and economic impact, enhance the importance of catalysis, allows real-time analysis for pollution prevention and provides inherently safer chemistry (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#F1" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Figure 1</a>) <a data-original-title="" data-placement="bottom" data-popover-content="#link3-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link3" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[3]. Without claiming to be exhaustive, in this review we report recently published representative synthetic applications that demonstrate the growing contribution of flow chemistry and microreactor technology in green and sustainable synthesis <a data-original-title="" data-placement="bottom" data-popover-content="#link4-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link4" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[4-7].</div>
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<a href="https://www.blogger.com/null" id="F1" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-1" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-1]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/figures/1860-5397-13-51-1.png?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-1" data-thumb="/bjoc/content/figures/1860-5397-13-51-1.png?max-width=90&background=FFFFFF" id="figure1" src="https://www.beilstein-journals.org/bjoc/content/figures/1860-5397-13-51-1.png?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="869" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Figure 1:</strong> Microreactor technologies and flow chemistry for a sustainable chemistry.</figcaption></figure></div>
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Review</h2>
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Flow microreactors: main features</h3>
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The peculiar properties of microreactors <a data-original-title="" data-placement="bottom" data-popover-content="#link5-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link5" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[8] derive from their small size and can be ascribed mainly to the following characteristics: a) fast mixing: in a flow microreactor, in striking contrast to batch conditions, mixing takes place by molecular diffusion so that a concentration gradient can be avoided; b) high surface-to-volume ratio: the microstructure of microreactors allows for a very rapid heat transfer enabling fast cooling, heating and, hence, precise temperature control; c) residence time: it is the period of time the solution of reactants spend inside the reactor, and it gives a measure of the reaction time. The residence time is strictly dependent on the characteristics of the reactor (i.e., length of the channels, volume), and on the flow rate. The residence time is one of the crucial factors to be considered in optimizing flow reactions, especially when unstable or short-lived reactive intermediates are concerned. Microreactor technology provides also several benefits. Safety benefits, because of the high efficiency in heat exchange, and avoided accumulation of unstable intermediates. Economy benefits, due to lower manufacturing and operating costs, reduced work-up procedures, use of less raw materials and solvents and reduced waste. Chemistry benefits associated to the use of microreactor technology are the improved yields and selectivities, the possibility to conduct reactions difficult or even impossible to perform in batch, and the use of reaction conditions that allow exploring new chemical windows <a data-original-title="" data-placement="bottom" data-popover-content="#link6-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link6" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[9].</div>
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Contribution of flash chemistry to green and sustainable synthesis</h3>
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The concept of flash chemistry as a “<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">field of chemical synthesis using flow microreactors where extremely fast reactions are conducted in a highly controlled manner to produce desired compounds with high selectivity</i>” was firstly introduced by Yoshida <a data-original-title="" data-placement="bottom" data-popover-content="#link7-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link7" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[10]. Flash chemistry can be considered a new concept in both organic and sustainable synthesis involving chemical transformations that are very difficult or practically impossible to conduct using conventional batch conditions. With the aim to show how flow microreactor technology and flash chemistry could contribute to the development of a sustainable organic synthesis, very recent examples have been selected and will be discussed here. In the context of green chemistry <a data-original-title="" data-placement="bottom" data-popover-content="#link8-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link8" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[11], protecting-group free organic synthesis has received particular attention in the last years, because of atom economy <a data-original-title="" data-placement="bottom" data-popover-content="#link9-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link9" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[12-15] and reduction of synthetic steps <a data-original-title="" data-placement="bottom" data-popover-content="#link10-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link10" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[16]. It has been demonstrated by Yoshida that protecting-group-free synthesis could be feasible using flash chemistry and microreactor technology <a data-original-title="" data-placement="bottom" data-popover-content="#link11-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link11" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[17,18]. Recently, Yoshida and co-workers developed flash methods for the generation of highly unstable carbamoyl anions, such as carbamoyllithium, using a flow microreactor system <a data-original-title="" data-placement="bottom" data-popover-content="#link12-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link12" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[19]. In particular, they reported that starting from different substituted carbamoyl chloride <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">1</b> and lithium naphthalenide (LiNp) it was possible to generate the corresponding carbamoyllithium <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">2</b>, that upon trapping with different electrophiles provided several amides and ketoamide <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">3</b>(<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S1" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 1</a>).</div>
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 1:</strong> A flow microreactor system for the generation and trapping of highly unstable carbamoyllithium species.</figcaption></figure></div>
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The use of an integrated microflow system allowed the preparation of functionalized α-ketoamides by a three-component reaction between carbamoyllithium, methyl chloroformate and organolithium compounds bearing sensitive functional groups (i.e., NO<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">2</span>, COOR, epoxide, carbonyl) (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S2" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 2</a>).</div>
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<a href="https://www.blogger.com/null" id="S2" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i2" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i2]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i2.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i2" data-thumb="/bjoc/content/inline/1860-5397-13-51-i2.svg?max-width=90&background=FFFFFF" id="scheme2" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i2.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="881" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 2:</strong> Flow synthesis of functionalized α-ketoamides.</figcaption></figure></div>
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It should be stressed that this kind of sequential transformations are practically impossible to perform using conventional batch chemistry because of the incompatibility of sensitive functional groups with organolithiums, and because of the high chemical and thermal instability of the intermediates.</div>
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In 2015 Yoshida reported another remarkable finding on the use of protecting-group-free organolithium chemistry. In particular, the flash chemistry approach was exploited for generating benzyllithiums bearing aldehyde or ketone carbonyl groups <a data-original-title="" data-placement="bottom" data-popover-content="#link13-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link13" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[20]. This reaction could be problematic for two reasons: a) the competing Wurtz-type coupling, (i.e., the coupling of benzyllithiums with the starting benzyl halides); b) the nucleophilic attack of organolithium species to aldehyde or ketone carbonyl groups (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S3" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 3</a>).</div>
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<a href="https://www.blogger.com/null" id="S3" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i3" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 3:</strong> Reactions of benzyllithiums.</figcaption></figure></div>
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The authors reported that the extremely fast micromixing avoided undesired Wurtz-type coupling <a data-original-title="" data-placement="bottom" data-popover-content="#link14-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link14" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[21,22]. It is well known, that competitive reactions can be controlled or even avoided under fast micromixing <a data-original-title="" data-placement="bottom" data-popover-content="#link15-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link15" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[23-27]. Moreover, high-resolution residence time control was essential for survival of carbonyl groups. In fact, this transformation can be achieved only with a residence time of 1.3 ms at −78 °C. Under these flow conditions, the aldehyde or ketone carbonyl moiety can survive the nucleophilic organolithium attack. Remarkably, the flow microreactor system allowed also the generation of benzyllithiums at 20 °C, rather than under cryogenic (−95 °C) conditions adopted with a conventional batch protocol. In addition, THF could be used in place of mixed solvents (Et<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">2</span>O/THF/light petroleum). Under the optimized conditions, the reactions of benzyllithiums with different electrophiles, gave adduct products in good yields (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S4" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 4</a>).</div>
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<figure><img alt="[1860-5397-13-51-i4]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i4.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i4" data-thumb="/bjoc/content/inline/1860-5397-13-51-i4.svg?max-width=90&background=FFFFFF" id="scheme4" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i4.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="881" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 4:</strong> Trapping of benzyllithiums bearing carbonyl groups enabled by a flow microreactor. (Adapted with permission from <a data-original-title="" data-placement="bottom" data-popover-content="#link16-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link16" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[18], copyright 2015 The Royal Society of Chemistry).</figcaption></figure></div>
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Another useful aspect of the flash chemistry relies on the possibility to generate highly reactive intermediates, such as halomethyllithium carbenoids, that need to be used under internal-quenching technique in batch mode. In 2014, the first example of effective external trapping of a reactive chloromethyllithium (CML) has been reported <a data-original-title="" data-placement="bottom" data-popover-content="#link17-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link17" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[28]. α-Haloalkyllithiums are a useful class of organometallic reagents widely employed in synthetic chemistry. In fact, they allow the direct homologation of carbonyl compounds and imines leading to β-halo-alcohols and amines that are useful building blocks <a data-original-title="" data-placement="bottom" data-popover-content="#link18-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link18" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[29-31]. This work represents a remarkable example of flash chemistry, and has elements of sustainability considering that in batch macroreactors, in order to avoid metal-assisted α-elimination, in situ quenching, an excess of reagents, and very low temperature are required <a data-original-title="" data-placement="bottom" data-popover-content="#link19-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link19" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[32,33].</div>
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Running the reaction in a flow system at −40 °C, by using residence times between 0.18–0.31 s high yields of homologated products have been obtained under external quenching conditions (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S5" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 5</a>).</div>
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<a href="https://www.blogger.com/null" id="S5" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i5" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i5]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i5.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i5" data-thumb="/bjoc/content/inline/1860-5397-13-51-i5.svg?max-width=90&background=FFFFFF" id="scheme5" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i5.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="879" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 5:</strong> External trapping of chloromethyllithium in a flow microreactor system.</figcaption></figure></div>
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The results described above nicely show the potential, as green technology, of flow microreactor systems for synthetic processes involving highly unstable intermediates. Another nice example on the use of microreactor technology for the development of sustainable chemical processes, is represented by the direct introduction of the <i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">tert</i>-butoxycarbonyl group into organometallic reagents <a data-original-title="" data-placement="bottom" data-popover-content="#link20-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link20" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[34]. The reaction between organolithium reagents and di-<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">tert</i>-butyl dicarbonate run under flow conditions, allowed a straightforward preparation of several <i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">tert</i>-butyl esters. The use of a flow process resulted more efficient, versatile and sustainable compared to batch. Moreover, this operationally simple procedure complements well with the already available strategies for the preparation of <i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">tert</i>-butyl esters, avoiding the use of inflammable and explosive gaseous isobutylene <a data-original-title="" data-placement="bottom" data-popover-content="#link21-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link21" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[35], the use of harsh conditions <a data-original-title="" data-placement="bottom" data-popover-content="#link22-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link22" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[36], the use of peroxides <a data-original-title="" data-placement="bottom" data-popover-content="#link23-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link23" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[37], the use of toxic gas such as CO or transition metals <a data-original-title="" data-placement="bottom" data-popover-content="#link24-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link24" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[38-42]. The flow process, for the direct C-<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">tert</i>-butoxycarbonylation of organolithiums, has been optimized in a green solvent such as 2-MeTHF by a precise control of the residence time, and without using cryogenic conditions (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S6" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 6</a>). In addition, many organolithiums were generated from the corresponding halo compounds by a halogen/lithium exchange reaction using hexyllithium as a more sustainable base <a data-original-title="" data-placement="bottom" data-popover-content="#link25-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link25" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[43,44].</div>
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<a href="https://www.blogger.com/null" id="S6" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i6" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i6]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i6.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i6" data-thumb="/bjoc/content/inline/1860-5397-13-51-i6.svg?max-width=90&background=FFFFFF" id="scheme6" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i6.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="840" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 6:</strong> Scope for the direct <i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">tert</i>-butoxycarbonylation using a flow microreactor system.</figcaption></figure></div>
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The concept of flash chemistry has been successfully employed for outpacing fast isomerization reactions. The accurate control of the residence time, realized in a microreactor, could suppress or avoid isomerization of unstable intermediates. This is often unavoidable when the same reactions are run in batch mode <a data-original-title="" data-placement="bottom" data-popover-content="#link26-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link26" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[45-47].</div>
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Yoshida and Kim recently provided an astonishing example on the potential of flash chemistry in controlling fast isomerization of organolithiums <a data-original-title="" data-placement="bottom" data-popover-content="#link27-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link27" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[48]. The authors designed a chip microreactor (CMR), able to deliver a reaction time in the range of submilliseconds (0.33 ms) under cryogenic conditions. By using such an incredible short residence time, it was possible to overtake the very rapid anionic Fries rearrangement, and chemoselectively functionalize <i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">ortho</i>-lithiated aryl carbamates (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S7" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 7</a>).</div>
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<a href="https://www.blogger.com/null" id="S7" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i7" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i7]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i7.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i7" data-thumb="/bjoc/content/inline/1860-5397-13-51-i7.svg?max-width=90&background=FFFFFF" id="scheme7" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i7.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="863" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 7:</strong> Control of anionic Fries rearrangement reactions by using submillisecond residence time. (Adapted with permission <a data-original-title="" data-placement="bottom" data-popover-content="#link28-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link28" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[43], copyright 2016 American Association for the Advancement of Science).</figcaption></figure></div>
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This CMR has been developed choosing a fluoroethylene propylene–polymide film hybrid for fabrication because this material offers exceptional physical toughness at low temperature and high pressure as well as chemical inertness. The most relevant aspect of this microreactor, concerns the 3D design of the mixing zone (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#F2" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Figure 2</a>). The mixing efficiency was evaluated on the basis of computational fluids dynamics (CFD). The simulation results showed that serpentine 3D-structured channels (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#F2" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Figure 2</a>), possessing five turns after each mixing point in a total length of 1 mm, was able to deliver the highest mixing efficiency. The inner volume for the reactor was of 25 μL. This CMR provides mixing efficiency levels of 95% with a total flow rates of 7.5 mL/min corresponding to a residence time of about 0.3 milliseconds.</div>
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<figure><img alt="[1860-5397-13-51-2]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/figures/1860-5397-13-51-2.png?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-2" data-thumb="/bjoc/content/figures/1860-5397-13-51-2.png?max-width=90&background=FFFFFF" id="figure2" src="https://www.beilstein-journals.org/bjoc/content/figures/1860-5397-13-51-2.png?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="859" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Figure 2:</strong> Chip microreactor (CMR) fabricated with six layers of polyimide films. (Reproduced with permission from <a data-original-title="" data-placement="bottom" data-popover-content="#link29-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link29" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[43], copyright 2016 American Association for the Advancement of Science).</figcaption></figure></div>
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To show the potential use of this microdevice in organic synthesis, the synthesis of Afesal <a data-original-title="" data-placement="bottom" data-popover-content="#link30-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link30" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[49], a biologically active compound having anthelmintic activity was reported as application.</div>
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This outstanding result by Yoshida and Kim, demonstrates how microdevices and flash chemistry could contribute to the development of new sustainable synthetic strategies, and how microreactor technology could help in taming the reactivity of unstable species <a data-original-title="" data-placement="bottom" data-popover-content="#link31-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link31" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[50].</div>
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Contribution of continuous-flow metal-, organo-, and photocatalysis in green chemistry</h3>
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The development of continuous-flow catalysis is appealing because it combines the advantages of a catalytic reaction with the benefits of flow microreactors. Under homogeneous conditions a soluble catalyst, which flows through the reactor together with the reactants, is employed. At the end of the process, a separation step would be required in order to remove the catalyst and byproducts. On the other hand, heterogeneous catalysis is widely used in the synthesis of bulk and fine chemicals. In a continuous-flow process, the catalyst can be fixed on a suitable hardware, and the reaction mixture allowed to flow through the system. The use of recyclable catalysts in continuous-flow conditions represents an innovative strategy for the development of more environmentally friendly synthesis. In the last decade, organic photochemistry got a sort of renaissance, emerging as useful approach in modern sustainable and green synthesis.</div>
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Concerning the heterogeneous catalysis with palladium, practical procedures for recovering and reusing of the catalysts have been recently reported <a data-original-title="" data-placement="bottom" data-popover-content="#link32-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link32" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[51-53]. A versatile Pd-catalysed synthesis of polyfunctionalized biaryls, using a flow microreactor, has been recently reported by Yoshida <a data-original-title="" data-placement="bottom" data-popover-content="#link33-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link33" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[54]. Using the integrated microflow system reported in <a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S8" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 8</a>, arylboronic esters were prepared by a lithiation/borylation sequence, and used in a Suzuki–Miyaura coupling in a monolithic reactor. A remarkable aspect of the process was the use of an integrated supported monolithic Pd(0) catalyst that allowed to perform cross-coupling reactions in continuous flow mode (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S8" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 8</a>).</div>
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 8:</strong> Flow microreactor system for lithiation, borylation, Suzuki–Miyaura coupling and selected examples of products.</figcaption></figure></div>
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This integrated microflow system allow to handle the borylation of aryl halides (Ar<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">1</span>X), and the subsequent Suzuki–Miyaura coupling using different aryl halide (Ar<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">2</span>X). Without requiring the protection of sensitive functionalities, running the flow system using a residence time (<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">t</i><span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">R</span>) of about 4.7 min at a temperature above 100 °C, high yields of coupling products were obtained. Noteworthy, the Suzuki–Miyaura coupling did not require the use of a base. The authors applied the presented method to the synthesis of adapalene, used in the treatment of acne, psoriasis, and photoaging.</div>
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Fluorinated aromatic compounds are extremely important in agrochemical, pharmaceutical and medicinal fields <a data-original-title="" data-placement="bottom" data-popover-content="#link34-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link34" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[55-58]. Buchwald and co-workers suggested a telescoped homocatalysis procedure consisting of a three-step sequence (metalation, zincation and Negishi cross-coupling) which furnishes an easy access to a variety of functionalized 2-fluorobiaryl and heteroaryl products (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S9" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 9</a>) <a data-original-title="" data-placement="bottom" data-popover-content="#link35-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link35" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[59]. This strategy is rightfully considered green because it guarantees the employment of readily available and cheap starting materials, the safe handling of highly thermally unstable or dangerous intermediates, and the use of higher temperature with respect to the batch mode in which the proposed reactions have to be carried out at −78 °C.</div>
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<a href="https://www.blogger.com/null" id="S9" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i9" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i9]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i9.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i9" data-thumb="/bjoc/content/inline/1860-5397-13-51-i9.svg?max-width=90&background=FFFFFF" id="scheme9" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i9.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="847" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 9:</strong> Experimental setup for the flow synthesis of 2-fluorobi(hetero)aryls by directed lithiation, zincation, and Negishi cross-coupling. (Adapted with permission from <a data-original-title="" data-placement="bottom" data-popover-content="#link36-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link36" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[53], copyright 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim).</figcaption></figure></div>
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The use of 2-MeTHF as greener solvent, contributes to further validate the green procedure. The 2-MeTHF solutions of fluoroarenes <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">4</b> together with the hexane solution of <i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">n</i>-BuLi were pumped into the flow system at −40 °C. The generated organozinc intermediate meets the solution of haloarenes and the catalyst, leading to the formation of the desired products <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">5a–j</b> (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S9" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 9</a>). Noteworthy, the homogeneous catalysis requires only 1% of the XPhos-based palladium catalyst. A sonication bath was employed to prevent clogging and the reaction required a residence time of 15 min.</div>
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Next, they turned their attention to the arylation of fluoro-substituted pyridines. The regioselective lithiation of halopyridines with lithium diisopropylamide (LDA) was conducted under mild conditions on substrate <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">6</b>(<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S10" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 10</a>). The addition of a little amount of THF was necessary in order to avoid clogging and the tendency of the lithiated intermediate to eliminate.</div>
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<a href="https://www.blogger.com/null" id="S10" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i10" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i10]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i10.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i10" data-thumb="/bjoc/content/inline/1860-5397-13-51-i10.svg?max-width=90&background=FFFFFF" id="scheme10" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i10.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="880" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 10:</strong> Experimental setup for the coupling of fluoro-substituted pyridines. (Adapted with permission from <a data-original-title="" data-placement="bottom" data-popover-content="#link37-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link37" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[53], copyright 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim).</figcaption></figure></div>
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The optimized conditions were suitable for the functionalization of 2-fluoropyridine, 2,6- difluoropyridine and 4-(trifluoromethyl)pyridine leading to products <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">7a–g</b> reported in <a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S10" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 10</a>. Another promising field is the sustainable flow organocatalysis, and recently Pericàs reported an interesting synthesis and application of a recyclable immobilized analogue of benzotetramisole (BMT) used in a catalytic enantioselective Michael addition/cyclization reactions under continuous-flow conditions (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S11" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 11</a>) <a data-original-title="" data-placement="bottom" data-popover-content="#link38-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link38" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[60].</div>
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<a href="https://www.blogger.com/null" id="S11" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i11" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i11]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i11.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i11" data-thumb="/bjoc/content/inline/1860-5397-13-51-i11.svg?max-width=90&background=FFFFFF" id="scheme11" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i11.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="869" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 11:</strong> Continuous flow process setup for the preparation of <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">11</b> (Reproduced with permission from <a data-original-title="" data-placement="bottom" data-popover-content="#link39-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link39" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[54], copyright 2015 American Chemical Society).</figcaption></figure></div>
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Resin-bound catalyst <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">10</b> was swollen with dichloromethane in a medium-pressure chromatography column used as a reactor. Dichloromethane solutions of substrate <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">9</b> reacted with the mixed phenylacetic pivalic anhydride (deriving from phenylacetic acetic (<b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">8</b>) and pivaloyl chloride) inside the catalytic reactor producing the expected products <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">11</b>. This ingenious system was equipped with an in-line FTIR probe, for monitoring the transformation, and an in line liquid–liquid separator to avoid tedious work-up procedures, thus saving solvents, resources and optimizing work times. This system was demonstrated to work for 11 h with higher conversion and enantioselectivity (er >99.9%) in comparison to the batch mode <a data-original-title="" data-placement="bottom" data-popover-content="#link40-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link40" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[61]. Pericàs and co-workers taking advantage of the high catalytic activity, robustness and recyclability of the supported catalyst, performed also straightforward gram synthesis of target compounds.</div>
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In the context of photocatalysis and oxidations using flow microreactors <a data-original-title="" data-placement="bottom" data-popover-content="#link41-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link41" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[62,63], Noël reported a metal-free photocatalytic aerobic oxidation of thiols to disulfides under continuous-flow conditions <a data-original-title="" data-placement="bottom" data-popover-content="#link42-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link42" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[64]. Disulfides are useful molecules employed as drugs, anti-oxidants or pesticides as well as rubber vulcanizating agents <a data-original-title="" data-placement="bottom" data-popover-content="#link43-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link43" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[65]. Symmetric disulfides are generally obtained by oxidative coupling of thiols <a data-original-title="" data-placement="bottom" data-popover-content="#link44-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link44" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[66]. Noël and co-workers set up a microflow system equipped with a mass flow controller (MFC) able to introduce pure oxygen as the oxidant to oxidize a solution of thiol containing 1% of Eosin Y. The flow stream was exposed to white LED light in order to activate the reaction, and a dilution with pure EtOH was needed at the output to avoid clogging (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S12" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 12</a>). The residence time of 20 min guaranteed a limited irradiation time and high purity of the products.</div>
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<a href="https://www.blogger.com/null" id="S12" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i12" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i12]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i12.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i12" data-thumb="/bjoc/content/inline/1860-5397-13-51-i12.svg?max-width=90&background=FFFFFF" id="scheme12" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i12.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="888" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 12:</strong> Continuous-flow photocatalytic oxidation of thiols to disulfides.</figcaption></figure></div>
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The disulfides were obtained with excellent yields, and the process was executed on challenging thiols as in the case of disulfide <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">12</b> (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S12" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 12</a>), used as food flavour additive <a data-original-title="" data-placement="bottom" data-popover-content="#link45-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link45" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[67]. To demonstrate the usefulness of the flow methodology, and its applicability, the photocatalytic aerobic oxidation of a peptide to obtain oxytocin in continuous flow was reported (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S12" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 12</a>). Full conversion was achieved in water with 200 s of residence time.</div>
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Noël optimized, for the first time, a trifluoromethylation of aromatic heterocycles by continuous-flow photoredox catalysis. The process benefited from the use of microreactor technology and readily available photocatalysts. The process was also employable for perfluoroalkylation. The developed process occurred in less time with respect to batch mode, and under milder conditions. The set-up of the reactor allowed for the use of gaseous CF<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">3</span>I by means of a mass flow controller. Selected examples of trifluoroalkylated products are reported in <a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S13" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 13</a> <a data-original-title="" data-placement="bottom" data-popover-content="#link46-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link46" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[68].</div>
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<a href="https://www.blogger.com/null" id="S13" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i13" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i13]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i13.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i13" data-thumb="/bjoc/content/inline/1860-5397-13-51-i13.svg?max-width=90&background=FFFFFF" id="scheme13" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i13.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="861" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 13:</strong> Trifluoromethylation by continuous-flow photoredox catalysis.</figcaption></figure></div>
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Tranmer reported a “traceless reagents” chemistry with the continuous-flow photosynthesis of 6(5<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">H</i>)-phenanthridinones, poly(ADP-ribose) polymerase (PARP) inhibitors <a data-original-title="" data-placement="bottom" data-popover-content="#link47-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link47" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[69]. The relevance of the work resides in the use of green solvents, the absence of heavy metals, the use of convenient temperatures, and the increased safety by eliminating UV-exposure locating the UV lamp within the microreactor. Hazard of fires caused by the hot UV lamps approaching the auto-ignition temperature of flammable solvents, very often underestimated, is totally prevented thanks to a specific cooling system. 2-Halo-<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">N</i>-arylbenzamides were converted into 6(5<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">H</i>)-phenanthridinones by a photocyclization reaction. In order to run this step, a flow system with a photochemical reactor equipped with a medium pressure Hg lamp and 10 mL reactor coil, was employed. Good yields were obtained from different 2-chlorobenzamides disclosing that either electron-donating or electron withdrawing <i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">ortho</i>-substituents were tolerated (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S14" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 14</a>).</div>
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<a href="https://www.blogger.com/null" id="S14" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i14" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i14]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i14.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i14" data-thumb="/bjoc/content/inline/1860-5397-13-51-i14.svg?max-width=90&background=FFFFFF" id="scheme14" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i14.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="849" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 14:</strong> Flow photochemical synthesis of 6(5<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">H</i>)-phenanthridiones from 2-chlorobenzamides.</figcaption></figure></div>
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A metal- and catalyst-free arylation procedure carried out under continuous-flow conditions was recently reported by Fagnoni <a data-original-title="" data-placement="bottom" data-popover-content="#link48-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link48" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[70]. This photochemical process allowed for the preparation of a wide range of synthetic targets by Ar–Csp<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">3</span>, Ar–Csp<span style="border: 0px; bottom: 1ex; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; vertical-align: baseline;">2</span> and Ar–Csp bond-forming reactions. The use of a photochemical flow reactor, consisting of a polyfluorinated tube reactor wrapped around a 500 W Hg lamp, allowed to overcome batch limitations paving the way for metal-free arylation reactions via phenyl cations. Derivatives <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">14a–g</b> were prepared with this greener flow approach (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S15" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 15</a>) starting from mesitylene <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">13</b>, and haloarenes using short irradiation times (<6 h), and a 5:1 MeCN/H<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">2</span>O mixture.</div>
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<a href="https://www.blogger.com/null" id="S15" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i15" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i15]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i15.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i15" data-thumb="/bjoc/content/inline/1860-5397-13-51-i15.svg?max-width=90&background=FFFFFF" id="scheme15" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i15.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="863" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 15:</strong> Synthesis of biaryls <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">14a–g</b> under photochemical flow conditions.</figcaption></figure></div>
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The reported results show how photochemistry hold the potential to become a green tool for the development of sustainable photochemical flow synthesis.</div>
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Hazardous chemistry by using green and sustainable continuous-flow microreactors</h3>
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We have already shown how continuous-flow technology could play an important role in improving chemical processes <a data-original-title="" data-placement="bottom" data-popover-content="#link49-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link49" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[5,71], providing different advantages over traditional batch mode. However, the hazardous nature of some chemicals makes handling at conventional lab or industrial scale difficult. The use of microreactors and continuous-flow chemistry offers the possibility to perform reactions using dangerous or hazardous materials that cannot be used in batch mode. In other word, syntheses previously “forbidden” for safety reasons, such as those involving diazo compounds, hydrazine, azides, phosgene, cyanides and other hazardous chemicals could be performed with relatively low risk using flow technology <a data-original-title="" data-placement="bottom" data-popover-content="#link50-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link50" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[72-76].</div>
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Several research groups investigated this aspect, as highlighted by several available reviews <a data-original-title="" data-placement="bottom" data-popover-content="#link51-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link51" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[77,78]. Here we describe very recent reports with the aim to highlight the potential of flow chemistry in the field of hazardous chemistry under a greener perspective.</div>
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Diazo compounds are recognized as versatile reagents in organic synthesis. Nevertheless, diazo compounds are also considered highly energetic reagents <a data-original-title="" data-placement="bottom" data-popover-content="#link52-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link52" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[79,80]. For this reason, the in situ generation of such reagents has been investigated under flow conditions. Moody and co-workers reported a new method for the in situ generation of diazo compounds as precursors of highly reactive metal carbenes (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S16" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 16</a>) <a data-original-title="" data-placement="bottom" data-popover-content="#link53-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link53" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[81].</div>
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<a href="https://www.blogger.com/null" id="S16" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i16" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i16]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i16.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i16" data-thumb="/bjoc/content/inline/1860-5397-13-51-i16.svg?max-width=90&background=FFFFFF" id="scheme16" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i16.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="811" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 16:</strong> Flow oxidation of hydrazones to diazo compounds.</figcaption></figure></div>
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As reported in <a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S16" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 16</a>, diazo species <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">18</b> could be generated from simple carbonyls <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">15</b> and hydrazine (<b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">16</b>). Intermediate hydrazones <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">17</b> can be converted into the corresponding diazo compounds by oxidation using a recyclable oxidant based on <i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">N</i>-iodo-<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">p</i>-toluenesulfonamide potassium salt. The possibility to regenerate a functionalized resin by simple washing with aqueous KI<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">3</span>/KOH solution makes the process more sustainable. This method produces KI solution as waste, and it is an alternative way for the direct oxidation of hydrazones, that often requires the use of heavy metals such as HgO, Pb(OAc)<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">4</span> and AgO <a data-original-title="" data-placement="bottom" data-popover-content="#link54-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link54" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[82,83].</div>
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The diazo compounds could be collected as solution in dichloromethane at the output of the flow system, and obtained sufficiently pure for further use without requiring handling or isolation. Further mixing of solutions containing diazo derivatives to a solution containing a Rh(II) catalyst, and reactants such as amines, alcohols or aldehydes led to a wide range of products as reported in <a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S17" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 17</a>.</div>
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<a href="https://www.blogger.com/null" id="S17" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i17" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i17]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i17.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i17" data-thumb="/bjoc/content/inline/1860-5397-13-51-i17.svg?max-width=90&background=FFFFFF" id="scheme17" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i17.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="850" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 17:</strong> Synthetic use of flow-generated diazo compounds.</figcaption></figure></div>
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Ley’s group developed several continuous-flow approaches for generating diazo species from hydrazones <a data-original-title="" data-placement="bottom" data-popover-content="#link55-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link55" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[84,85]. Under flow conditions, diazo compounds were reacted with boronic acids in order to generate reactive allylic and benzylic boronic acids further employed for iterative C–C bond forming reactions <a data-original-title="" data-placement="bottom" data-popover-content="#link56-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link56" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[86]. The generation of unstable diazo species was possible using a cheap, recyclable and less toxic oxidant, MnO<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">2</span>. The flow stream was accurately monitored by in-line FTIR spectroscopy in order to maximize the formation of the diazo compound (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S18" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 18</a>) <a data-original-title="" data-placement="bottom" data-popover-content="#link57-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link57" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[87].</div>
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<a href="https://www.blogger.com/null" id="S18" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i18" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i18]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i18.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i18" data-thumb="/bjoc/content/inline/1860-5397-13-51-i18.svg?max-width=90&background=FFFFFF" id="scheme18" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i18.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="827" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 18:</strong> Ley’s flow approach for the generation of diazo compounds.</figcaption></figure></div>
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Starting from this initial investigation, Ley and co-workers developed an elegant application of this strategy for a sequential formation of up to three C–C bonds in sequence, by an iterative trapping of boronic acid species. The sequence starts with the reaction of diazo compound <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">20</b>, generated under flow conditions, and boronic acid <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">19</b> (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S19" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 19</a>). Further sequential coupling with diazo compounds <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">21</b> and <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">22</b> led to boronates <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">23</b> or protodeboronated products <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">24</b> at the end of the sequence (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S19" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 19</a>).</div>
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<figure><img alt="[1860-5397-13-51-i19]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i19.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i19" data-thumb="/bjoc/content/inline/1860-5397-13-51-i19.svg?max-width=90&background=FFFFFF" id="scheme19" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i19.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="857" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 19:</strong> Iterative strategy for the sequential coupling of diazo compounds.</figcaption></figure></div>
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With the aim to exploit the versatility of this approach, Ley and co-workers reported the allylations of carbonyl electrophiles such as aldehydes using the above reported strategy for the generation of allylboronic acids. The flow protocol considers the reaction of diazo compounds <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">25</b> (generated in flow) with boronic acid <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">26</b> and aldehyde <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">27</b> (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S20" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 20</a>). By this new iterative coupling it was possible to obtain alcohols as products. The usefulness of the method was demonstrated with the preparation in good yield (60%) of a precursor of the natural product bakuchiol <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">28</b> (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S20" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 20</a>) <a data-original-title="" data-placement="bottom" data-popover-content="#link58-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link58" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[88].</div>
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<a href="https://www.blogger.com/null" id="S20" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i20" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i20]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i20.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i20" data-thumb="/bjoc/content/inline/1860-5397-13-51-i20.svg?max-width=90&background=FFFFFF" id="scheme20" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i20.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="852" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 20:</strong> Integrated synthesis of Bakuchiol precursor via flow-generated diazo compounds.</figcaption></figure></div>
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The microreactor technology offers the advantage to handle hazardous components such as hydrazine and molecular oxygen, which represent alternative reagents for selective reduction of C=C double bonds. In fact, combination of hydrazine hydrate (N<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">2</span>H<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">4</span>·H<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">2</span>O) and O<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">2</span> provide diimide (HN=NH) as reducing agent. Nevertheless, this strategy is rarely used in traditional batch chemistry for safety reason. Kappe and co-workers recently developed a reduction of the alkene to the corresponding alkane, by a catalyst-free generation of diimide by oxidation of hydrazine monohydrate (N<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">2</span>H<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">4</span>·H<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">2</span>O) with molecular oxygen <a data-original-title="" data-placement="bottom" data-popover-content="#link59-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link59" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[89,90]. The flow system set-up is reported in <a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S21" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 21</a><i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">,</i> and consists in a HPLC pump for delivering the alkene and hydrazine monohydrate, while O<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">2</span> was delivered by a mass-flow controller (MFC) from a standard compressed-gas cylinder. After combination of the reagent streams, the resulting segmented flow was pumped through a heated residence unit (RTU) consisting in a fluorinated tube with low gas permeability (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S21" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 21</a>).</div>
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<a href="https://www.blogger.com/null" id="S21" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i21" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i21]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i21.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i21" data-thumb="/bjoc/content/inline/1860-5397-13-51-i21.svg?max-width=90&background=FFFFFF" id="scheme21" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i21.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="872" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 21:</strong> Kappe’s continuous-flow reduction of olefines with diimide.</figcaption></figure></div>
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The flow system reported in <a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S21" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 21</a> was able to reduce alkenes with high yields and selectivity by using residence times in the range of 10 to 30 min at 100 °C, and by employing a slight excess of hydrazine. Importantly, this strategy is compatible with sensitive functional groups such as silyl ether, halogenes, and benzyl groups. A very nice application of this approach was the highly selective reduction of artemisinic acid to dihydroartemisinic acid, which are of interest in the synthesis of the antimalarial drug artemisinin. This industrially relevant reduction was executed by using O<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">2</span> at 20 bar, four residence units at 60 °C and consecutive feedings with N<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">2</span>H<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">4</span>·H<span style="border: 0px; font-size: 0.7em; height: 0px; line-height: 1; margin: 0px; outline: 0px; padding: 0px; position: relative; top: 0.5ex; vertical-align: baseline;">2</span>O in order to obtain full conversion in dihydroartemisinic acid (<b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">29</b>, DHAA, <a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S22" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 22</a>).</div>
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<figure><img alt="[1860-5397-13-51-i22]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i22.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i22" data-thumb="/bjoc/content/inline/1860-5397-13-51-i22.svg?max-width=90&background=FFFFFF" id="scheme22" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i22.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="869" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 22:</strong> Multi-injection setup for the reduction of artemisinic acid.</figcaption></figure></div>
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Continuous-flow sustainable production of APIs</h3>
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With the aim to demonstrate the potential of microreactor technology and flow chemistry in sustainable synthesis, recent outstanding “proof of concepts” will be described. Kobayashi and co-workers reported a multistep continuous-flow synthesis of a drug target via heterogeneous catalysis. The developed process not requiring any isolation of intermediates, separation of the catalyst or other work-up procedures can be considered sustainable <a data-original-title="" data-placement="bottom" data-popover-content="#link60-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link60" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[91]. The syntheses of (<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">S</i>)-rolipram and a γ-aminobutyric acid (GABA) derivative were accomplished. Readily available starting materials and columns containing chiral heterogeneous catalysts to produce enantioenriched materials were employed. It is worth mentioning that this work represents a very nice example on the use of chiral catalysis in a multistep flow synthesis of a drug target on gram scale. The multistep synthesis of (<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">S</i>)-rolipram reported in <a href="https://www.beilstein-journals.org/bjoc/articles/13/51#S23" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Scheme 23</a> begins from a benzaldehyde derivative which undergoes a Henry-type reaction with nitromethane in the first flow step (Flow I). The resulting nitroalkene undergoes an asymmetric addition catalyzed by a supported PS–(<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">S</i>)-pybox–calcium chloride catalyst at 0 °C using two columns (Flow II). This is the enantio-determining step of the process. The stereochemistry of the adduct can be simply switched to the opposite enantiomer, by using the enantiomeric supported catalyst PS–(<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">R</i>)-pybox–calcium chloride. The enantiomeric excess of the products was about 96%. Two more steps consisting in a Pd-catalyzed hydrogenation reaction and a decarboxylation (Flow III and Flow IV) led to the target (<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">S</i>)-rolipram in 50% overall yield. The systems was designed in order to keep the level of the palladium in solution as low as possible (<0.01 ppm).</div>
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<a href="https://www.blogger.com/null" id="S23" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><a href="https://www.blogger.com/null" id="1860-5397-13-51-i23" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"></a><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figure><img alt="[1860-5397-13-51-i23]" class="js-gallery-id__1-item figure__image" data-src="/bjoc/content/inline/1860-5397-13-51-i23.svg?scale=2.0&max-width=1024&background=FFFFFF" data-sub-html="#caption-1860-5397-13-51-i23" data-thumb="/bjoc/content/inline/1860-5397-13-51-i23.svg?max-width=90&background=FFFFFF" id="scheme23" src="https://www.beilstein-journals.org/bjoc/content/inline/1860-5397-13-51-i23.svg?max-width=637&background=FFFFFF" style="border: none; font-size: 13.92px; margin: 0px; max-width: 100%; outline: 0px; padding: 0px;" width="893" /><div style="border: 0px; font-size: 13.92px; margin-bottom: 1.5em; outline: 0px; padding: 0px;">
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Scheme 23:</strong> Flow reactor system for multistep synthesis of (<i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">S</i>)-rolipram. Pumps are labelled a, b, c, d and e; Labels A, B, C, D, E and F are flow lines. X are molecular sieves; Y is Amberlyst 15Dry; Z is Celite. (Reproduced with permission from <a data-original-title="" data-placement="bottom" data-popover-content="#link61-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link61" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[84], copyright 2015 Nature Publishing Group).</figcaption></figure></div>
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Another outstanding proof of concept, which demonstrates the potential of flow chemistry for sustainable pharmaceutical manufacturing, has been recently reported by Jensen and his research team. The research team set up a compact and reconfigurable manufacturing platform for the continuous-flow synthesis and formulation of active pharmaceutical ingredients (APIs) <a data-original-title="" data-placement="bottom" data-popover-content="#link62-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link62" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[92]. The “mini” plant (reported in <a href="https://www.beilstein-journals.org/bjoc/articles/13/51#F3" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Figure 3</a>) was very compact in size [1.0 m × 0.7 m × 1.8 m, (W × L × H)], and low-weighing (about 100 kg) and was able to perform complex multistep synthesis, work-up procedures as well as purification operations such as crystallization. This platform was also equipped with devices for real-time monitoring and final formulation of high purity APIs. For the preparation of target molecules, commercially available starting materials were employed. The platform was tested for the production and supply of hundreds to thousands doses per day of diphenhydramine hydrochloride, lidocaine hydrochloride, diazepam and fluoxetine hydrochloride.</div>
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Remarkably, for future applications of the platform, the produced medicines also met the U.S. Pharmacopeia standards.</div>
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Figure 3:</strong> Reconfigurable modules and flowcharts for API synthesis. (Reproduced with permission from <a data-original-title="" data-placement="bottom" data-popover-content="#link63-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link63" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[85], copyright 2016 American Association for the Advancement of Science).</figcaption></figure></div>
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The future use of this kind of platform would concern the “on-demand” production or the “instantaneous” production of short-lived pharmaceuticals (<a href="https://www.beilstein-journals.org/bjoc/articles/13/51#F4" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;">Figure 4</a>). Other advantageous concerns of this reconfigurable platform are the lower production costs, the higher safety, the automation (computer controlled processes), the reduced waste (production could be done where is needed and in the right amount).</div>
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<figcaption><strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Figure 4:</strong> Reconfigurable system for continuous production and formulation of APIs. (Reproduced with permission from <a data-original-title="" data-placement="bottom" data-popover-content="#link64-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link64" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[85], copyright 2016 American Association for the Advancement of Science).</figcaption></figure></div>
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Conclusion</h2>
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Flow chemistry and manufacturing engineering have become largely acknowledged as viable and very often superior alternative to batch processing. Continuous-flow techniques offer increased safety, scalability, reproducibility, automation, reduced waste and costs, and accessibility to a wide range of new chemical possibilities, seldom not accessible through classic batch chemistry. All those benefits are even more noteworthy and outstanding than what they might seem, because they widely fulfil most of the green chemistry principles. In this short overview, we tried to highlight progresses and potential of flow chemistry in the field of sustainable synthesis. Thus, it is expected that flow chemistry and microreactor technology could deeply change the way to perform sustainable chemical production in the near future <a data-original-title="" data-placement="bottom" data-popover-content="#link65-content" data-toggle="popover" data-trigger="focus" href="https://www.blogger.com/null" id="link65" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;" tabindex="0" title=""></a>[93].</div>
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References</h2>
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How to cite this article:<br />Fanelli, F.; Parisi, G.; Degennaro, L.; Luisi, R. <i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Beilstein J. Org. Chem.</i> <b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">2017,</b> <i style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">13,</i> 520–542. <a href="https://doi.org/10.3762%2Fbjoc.13.51" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;" target="_blank">doi:10.3762/bjoc.13.51</a></div>
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<span lang="en-us" style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><span style="border: 0px; color: grey; font-family: Arial; font-size: large; margin: 0px; outline: 0px; padding: 0px;">Department of Pharmacy – Drug Sciences</span></span></div>
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<span style="border: 0px; font-family: Arial; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Welcome to my personal web page!!</b></span></div>
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<span style="border: 0px; font-family: Arial; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">As an organic chemist I’m involved in the development of new sustainable synthetic methodologies for the construction of new molecules with defined stereochemistry and functional properties.</span></div>
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<span style="border: 0px; font-family: Arial; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">Jointly with my coworkers we are involved in three main research themes:</span></div>
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<span style="border: 0px; font-family: Arial; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><span class="style_4" style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">1. Heterosubstituted Organolithiums</span>.</b> We mainly explore the reactivity of lithiated <span class="style_5" style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">3,4,5,6-membered N,S,O-heterocycles (aziridines, azetidines, oxazetidines, thietanes, oxazolines, piperazines, morfolines) </span>and their utility in stereoselective synthesis. Our approach is focused in establishing the chemical and configurational stability of the lithiated intermediates as well as their structure in solution by using modern spectrometric and spectroscopic techniques such as in line -IR, in line-MS, NMR and DOSY.</span></div>
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<span style="border: 0px; font-family: Arial; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><br /><b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><span class="style_6" style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">2. Microreactor Technology and Flow-Chemistry</span>.</b> With the aim to design more sustainable synthetic processes, we set up, at the Depatment of Pharmacy, a well equipped “flow chemistry laboratory” named FLAME-Lab, for the development of continuous-flow microreactor-mediated organometallic and organocatalytic synthesis in both homegenous and heterogenous conditions.</span></div>
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<span style="border: 0px; font-family: Arial; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><b style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;"><span class="style_6" style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">3. Molecular Dynamics</span>. </b>As a “curiosity driven” research activity, we investigate the dynamic behavior of small molecules that could function as molecular switches with “on-off” states and as versatile scaffolds useful in catalysis and in “dynamic-controlled and predictable reactivity”.</span></div>
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Assistant Professor</div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-26435576316128776942017-09-17T15:28:00.001+05:302017-09-17T15:28:46.550+05:30Ex Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates<div dir="ltr" style="text-align: left;" trbidi="on">
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A convenient transformation of phenols into the corresponding aryl fluorosulfates is presented: the first protocol to completely circumvent direct handling of gaseous sulfuryl fluoride (SO<span style="font-size: 0.8em; line-height: 0.8em; vertical-align: -0.4em;">2</span>F<span style="font-size: 0.8em; line-height: 0.8em; vertical-align: -0.4em;">2</span>). The proposed method employs 1,1′-sulfonyldiimidazole as a precursor to generate near-stoichiometric amounts of SO<span style="font-size: 0.8em; line-height: 0.8em; vertical-align: -0.4em;">2</span>F<span style="font-size: 0.8em; line-height: 0.8em; vertical-align: -0.4em;">2</span> gas using a two-chamber reactor. With NMR studies, it was shown that this <i>ex situ</i> gas evolution is extremely rapid, and a variety of phenols and hydroxylated heteroarenes were fluorosulfated in good to excellent yields.</div>
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<span class="hlFld-Title"><i>Ex Situ</i> Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates</span></h1>
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<span class="hlFld-ContribAuthor" style="white-space: nowrap;"><span class="hlFld-ContribAuthor" style="white-space: normal;"><a href="http://pubs.acs.org/author/Veryser%2C+Cedrick" id="authors" style="border-bottom: 1px dotted rgb(51, 102, 153); font-size: 1em; text-decoration-line: none;">Cedrick Veryser</a></span><a class="ref" href="http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b02522?utm_content=bufferd3ad9&utm_medium=social&utm_source=twitter.com&utm_campaign=buffer#notes-2" style="color: #336699; text-decoration-line: none;">‡</a><span class="orcid-link-icon"> <a href="http://orcid.org/0000-0001-9076-3623" style="color: #336699; text-decoration-line: none;" target="_blank"><img src="http://pubs.acs.org/templates/jsp/images/orcid.png" style="border: 0px; max-width: none; vertical-align: middle;" /></a></span>, </span><span class="hlFld-ContribAuthor" style="white-space: nowrap;"><span class="hlFld-ContribAuthor" style="white-space: normal;"><a href="http://pubs.acs.org/author/Demaerel%2C+Joachim" id="authors" style="border-bottom: 1px dotted rgb(51, 102, 153); font-size: 1em; text-decoration-line: none;">Joachim Demaerel</a></span><a class="ref" href="http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b02522?utm_content=bufferd3ad9&utm_medium=social&utm_source=twitter.com&utm_campaign=buffer#notes-2" style="color: #336699; text-decoration-line: none;">‡</a>, </span><span class="hlFld-ContribAuthor" style="white-space: nowrap;"><span class="hlFld-ContribAuthor" style="white-space: normal;"><a href="http://pubs.acs.org/author/Bieliunas%2C+Vidmantas" id="authors" style="border-bottom: 1px dotted rgb(51, 102, 153); font-size: 1em; text-decoration-line: none;">Vidmantas Bieliu̅nas</a></span>, </span><span class="hlFld-ContribAuthor" style="white-space: nowrap;"><span class="hlFld-ContribAuthor" style="white-space: normal;"><a href="http://pubs.acs.org/author/Gilles%2C+Philippe" id="authors" style="border-bottom: 1px dotted rgb(51, 102, 153); font-size: 1em; text-decoration-line: none;">Philippe Gilles</a></span>, and </span><span class="hlFld-ContribAuthor" style="white-space: nowrap;"><span class="hlFld-ContribAuthor" style="white-space: normal;"><a href="http://pubs.acs.org/author/de+Borggraeve%2C+Wim+M" id="authors" style="border-bottom: 1px dotted rgb(51, 102, 153); font-size: 1em; text-decoration-line: none;">Wim M. De Borggraeve</a></span><a class="ref" href="http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b02522?utm_content=bufferd3ad9&utm_medium=social&utm_source=twitter.com&utm_campaign=buffer#cor1" style="color: #336699; text-decoration-line: none;"><span style="font-size: 0.8em; line-height: 0.8em; vertical-align: 0.4em;">*</span></a><span class="orcid-link-icon"> <a href="http://orcid.org/0000-0001-7813-6192" style="color: #336699; text-decoration-line: none;" target="_blank"><img src="http://pubs.acs.org/templates/jsp/images/orcid.png" style="border: 0px; max-width: none; vertical-align: middle;" /></a></span></span></div>
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Molecular Design and Synthesis, Department of Chemistry, <span class="institution">KU Leuven</span>, Celestijnenlaan 200F, Box 2404, 3001 Leuven, <span class="country">Belgium</span></div>
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<cite>Org. Lett.</cite>, Article ASAP</div>
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<strong>DOI: </strong>10.1021/acs.orglett.7b02522</div>
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*E-mail: <a href="mailto:wim.deborggraeve@kuleuven.be" style="color: #336699; text-decoration-line: none;">wim.deborggraeve@kuleuven.be</a>.</div>
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<span style="font-family: Helvetica, Arial, sans-serif;"><span style="font-size: 14px;"><a href="http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b02522?utm_content=bufferd3ad9&utm_medium=social&utm_source=twitter.com&utm_campaign=buffer">http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b02522?utm_content=bufferd3ad9&utm_medium=social&utm_source=twitter.com&utm_campaign=buffer</a></span></span></div>
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4-fluoro-[1,1'-biphenyl]-4-yl sulfurofluoridate (compound 1) </div>
<div class="articleBody_abstractText" style="font-family: Helvetica, Arial, sans-serif; font-size: 14px; line-height: 1.6em; margin-bottom: 1.5em; padding: 0pt; width: 610px; word-wrap: break-word;">
General procedure A was followed using 192 mg of 4-fluoro-4’-hydroxybiphenyl (98 wt%, 1.0 mmol,
1.0 eq.). The crude reaction mixture was purified by solid-phase flash column chromatography on
silicagel (heptane, 100%). The title compound was obtained as a white solid (258 mg, 96%).
Rf = 0.39 (heptane/ethyl acetate, 9/1). Melting point = 47 – 49 °C. </div>
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1
H NMR (400 MHz, CDCl3): 7.62 (d,
J = 8.5 Hz, 1H), 7.52 (dd, J = 8.1, 5.5 Hz, 1H), 7.41 (d, J = 8.5 Hz, 1H), 7.16 (t, J = 8.5 Hz, 1H). </div>
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13C NMR
(101 MHz, CDCl3): δ 163.05 (d, J = 247.9 Hz), 149.51, 141.17, 135.55 (d, J = 3.3 Hz), 129.06, 128.98,
121.42, 116.13 (d, J = 21.6 Hz).</div>
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19F NMR (376 MHz, CDCl3): δ 37.18, -114.68 (m).</div>
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IR (neat) cm-1
: 1437,
1232, 921, 815. </div>
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CHN: calculated for C12H8F2O3S: C 53.33%, H 2.98%, N 0.00%; found: C 53.43%, H 3.26%,
N 0.00%.</div>
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<a href="http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.7b02522/suppl_file/ol7b02522_si_001.pdf">////////</a>//<a href="http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.7b02522/suppl_file/ol7b02522_si_001.pdf">///</a></div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-86985025517341697902017-09-17T15:16:00.001+05:302017-09-17T15:16:03.020+05:302,5-Bis(morpholinomethyl)furan<div dir="ltr" style="text-align: left;" trbidi="on">
<br />
2,5-Bis(morpholinomethyl)furan, 11<br />
<br />
Yield 98%, 1H NMR (CDCl3) = 6.13 (s, 2H), 3.70 (m, 8H), 3.51 (s, 4H), 2.45 (m, 8H);<br />
<br />
13C NMR (CDCl3) = 150.9, 109.7, 66.8, 55.3, 53.2 ppm.<br />
<br />
m/z HRMS (ESI) Calcd. for C14H22N2O3 [M+H]: 267.1703. Found 267.1703.<br />
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<div style="background-color: white; color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
<h4 class="itemtitle" style="color: #d5000b; font-family: Arial, Tahoma, Helvetica, FreeSans, sans-serif; font-size: 26px; font-stretch: normal; font-weight: normal; line-height: normal; margin: 0px; position: relative;">
<a data-mce-href="http://feeds.rsc.org/~r/rss/GC/~3/UhwMpS-2lRs/C7GC02211E" href="http://feeds.rsc.org/~r/rss/GC/~3/UhwMpS-2lRs/C7GC02211E" style="color: #b22223; text-decoration-line: none;">Efficient route for the construction of polycyclic systems from bioderived HMF</a> </h4>
</div>
<div style="background-color: white; color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
<i><b>Green Chem.</b></i>, 2017, Advance Article<br /><b>DOI</b>: 10.1039/C7GC02211E, Paper</div>
<div style="background-color: white; color: #333333; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px;">
F. A. Kucherov, K. I. Galkin, E. G. Gordeev, V. P. Ananikov<br />Efficient one-pot synthesis of tricyclic compounds from biobased 5-hydroxymethylfurfural (HMF) is described using a [4 + 2] cycloaddition reaction.</div>
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Efficient route for the construction of polycyclic systems from bioderived HMF</h2>
</div>
<div class="article__authors">
<span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AF.%20A.%20Kucherov" href="http://pubs.rsc.org/en/results?searchtext=Author%3AF.%20A.%20Kucherov" style="color: #b22223; text-decoration-line: none;">F. A. Kucherov</a>,<sup>a</sup> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AK.%20I.%20Galkin" href="http://pubs.rsc.org/en/results?searchtext=Author%3AK.%20I.%20Galkin" style="color: #b22223; text-decoration-line: none;">K. I. Galkin</a>,<sup>a</sup> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AE.%20G.%20Gordeev" href="http://pubs.rsc.org/en/results?searchtext=Author%3AE.%20G.%20Gordeev" style="color: #b22223; text-decoration-line: none;">E. G. Gordeev</a><sup>a</sup> and </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AV.%20P.%20Ananikov" href="http://pubs.rsc.org/en/results?searchtext=Author%3AV.%20P.%20Ananikov" style="color: #b22223; text-decoration-line: none;">V. P. Ananikov</a>*<sup>a</sup> </span></div>
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<a class="drawer__handle" data-mce-href="http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C7GC02211E?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#" href="http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C7GC02211E?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#" style="color: #b22223; text-decoration-line: none;"> Author affiliations</a><br /><div class="drawer__content">
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*Corresponding authors</div>
<div class="article__author-affiliation">
<sup>a</sup>Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991, Russia<br /><b>E-mail:</b> <a data-mce-href="mailto:val@ioc.ac.ru" href="mailto:val@ioc.ac.ru" style="color: #b22223; text-decoration-line: none;" title="val@ioc.ac.ru">val@ioc.ac.ru</a><br /><b>Web:</b> http://AnanikovLab.ru</div>
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<a data-mce-href="http://www.rsc.org/suppdata/c7/gc/c7gc02211e/c7gc02211e1.pdf" href="http://www.rsc.org/suppdata/c7/gc/c7gc02211e/c7gc02211e1.pdf" style="background-color: white; color: #b22223; font-family: Georgia, "Times New Roman", "Bitstream Charter", Times, serif; font-size: 16px; text-decoration-line: none;">//////</a><span style="background-color: white; color: #333333; font-family: georgia, "times new roman", "bitstream charter", times, serif; font-size: 16px;">////</span></div>
DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-59733201154385066882017-07-19T19:11:00.003+05:302017-07-19T19:11:43.121+05:30Iron-catalyzed dehydrogenation reactions and their applications in sustainable energy and catalysis<div dir="ltr" style="text-align: left;" trbidi="on">
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<img data-mce-src="http://drugapprovalsint.com/wp-content/uploads/2017/07/STR1-2.gif" src="http://drugapprovalsint.com/wp-content/uploads/2017/07/STR1-2.gif" style="height: auto; margin-bottom: 10px; margin-top: 8px; max-width: 100%;" /></div>
<div style="padding: 0px;">
Iron-catalyzed dehydrogenation reactions and their applications in sustainable energy and catalysis</div>
</div>
<div>
<i><b>Catal. Sci. Technol.</b></i>, 2017, Advance Article<br /><b>DOI</b>: 10.1039/C7CY00879A, Minireview</div>
<div>
Ekambaram Balaraman, Avanashiappan Nandakumar, Garima Jaiswal, Manoj K. Sahoo<br />This review article describes recent developments of iron-based acceptorless dehydrogenation (AD) reactions of fundamentally important feedstock, as a route to sustainable chemical synthesis and energy storage applications<a class="list__item-link" data-mce-href="http://pubs.rsc.org/en/journals/journal/cy" href="http://pubs.rsc.org/en/journals/journal/cy" style="color: #222222;"><span class="list__image-col"><img alt="" class="list__item-img" data-mce-src="http://pubs.rsc.org/en/Image/Get?imageInfo.ImageType=CoverIssue&imageInfo.ImageIdentifier.SerCode=CY&imageInfo.ImageIdentifier.IssueId=CY007014" height="88" id="imgLoader" src="http://pubs.rsc.org/en/Image/Get?imageInfo.ImageType=CoverIssue&imageInfo.ImageIdentifier.SerCode=CY&imageInfo.ImageIdentifier.IssueId=CY007014" style="height: auto; margin-bottom: 10px; margin-top: 8px; max-width: 100%;" title="Journal cover: Catalysis Science & Technology" /></span></a></div>
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Catalysis Science & Technology</h3>
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Iron-catalyzed dehydrogenation reactions and their applications in sustainable energy and catalysis</h2>
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<span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AEkambaram%20Balaraman" href="http://pubs.rsc.org/en/results?searchtext=Author%3AEkambaram%20Balaraman" style="color: #222222;">Ekambaram Balaraman</a>,*<span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">a</span><span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">b</span> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AAvanashiappan%20Nandakumar" href="http://pubs.rsc.org/en/results?searchtext=Author%3AAvanashiappan%20Nandakumar" style="color: #222222;">Avanashiappan Nandakumar</a>,*<span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">a</span> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AGarima%20Jaiswal" href="http://pubs.rsc.org/en/results?searchtext=Author%3AGarima%20Jaiswal" style="color: #222222;">Garima Jaiswal</a><span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">a</span><span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">b</span> and </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AManoj%20K.%20Sahoo" href="http://pubs.rsc.org/en/results?searchtext=Author%3AManoj%20K.%20Sahoo" style="color: #222222;">Manoj K. Sahoo</a><span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">a</span><span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">b</span> </span></div>
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*Corresponding authors</div>
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<span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">a</span>Catalysis Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune 411008, India<br /><b>E-mail:</b> <a data-mce-href="mailto:eb.raman@ncl.res.in" href="mailto:eb.raman@ncl.res.in" style="color: #222222;" title="eb.raman@ncl.res.in">eb.raman@ncl.res.in</a></div>
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<span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">b</span>Academy of Scientific and Innovative Research (AcSIR), New Delhi 110 025, India</div>
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Inspired by nature, chemists have designed new catalysts in the pursuit of selective bond activation and chemical transformations. Emergent biological systems often use earth-abundant first-row transition elements as catalytically active sites to facilitate specific and highly selective chemical processes. The design of a new catalytic system based on abundant and inexpensive catalysts, particularly the iron-based catalysts, for fundamentally significant synthetic transformations under environmentally benign conditions is an important paradigm in chemical synthesis. In recent times, iron-based catalytic systems have shown unprecedented reactivity in the acceptorless dehydrogenation reactions of feedstock chemicals, with the liberation of molecular hydrogen as the by-product, and have enabled greener chemical synthetic methods and alternative energy storage systems. Indeed, it has been demonstrated that the proper design of iron catalysts by judiciously choosing ligands, can aid in the development of new sustainable energy storage systems and catalysis. This tutorial review focuses on the recent development of iron-based dehydrogenation reactions of fundamentally important feedstock, as a route to sustainable chemical synthesis and energy storage applications. The emerging area of the iron-based dehydrogenation strategy provides an opportunity to make industrially applicable, cost-effective and environmentally benign catalytic systems</div>
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<img alt="eb.raman@" class="" data-mce-src="http://academic.ncl.res.in/ep_admin/images/profile/eb.raman_136.JPG" height="732" src="http://academic.ncl.res.in/ep_admin/images/profile/eb.raman_136.JPG" style="height: auto; margin-bottom: 10px; margin-top: 8px; max-width: 100%;" width="794" /></div>
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<span class="proffName">Dr.Ekambaram Balaraman</span><br />Catalysis Division<br />CSIR-National Chemical Laboratory</div>
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<span lang="EN-US"> </span><span lang="EN-US"><a data-mce-href="mailto:eb.raman@ncl.res.in" href="mailto:eb.raman@ncl.res.in" style="color: #222222;">eb.raman@ncl.res.in</a></span>; <span lang="EN-US"><a data-mce-href="mailto:balaramanekambaram@gmail.com" href="mailto:balaramanekambaram@gmail.com" style="color: #222222;">balaramanekambaram@gmail.com</a></span></div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-24325075101287628412017-06-03T16:04:00.001+05:302017-06-03T16:04:29.707+05:30 Synthesis of 2-substituted quinazolines by CsOH-mediated direct aerobic oxidative cyclocondensation of 2-aminoarylmethanols with nitriles in air<div dir="ltr" style="text-align: left;" trbidi="on">
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<i><b>Green Chem.</b></i>, 2017, Advance Article<br /><b>DOI</b>: 10.1039/C7GC00977A, Communication</div>
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Song Yao, Kaijing Zhou, Jiabing Wang, Hongen Cao, Lei Yu, Jianzhang Wu, Peihong Qiu, Qing Xu<br />An atom-efficient synthesis of 2-substituted quinazolines is developed by a CsOH-mediated aerobic oxidative reaction of 2-aminoarylmethanols and nitriles in air.</div>
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<a href="http://feeds.rsc.org/~r/rss/GC/~3/kmj6zvYBtQY/C7GC00977A" style="color: #000099;">Synthesis of 2-substituted quinazolines by CsOH-mediated direct aerobic oxidative cyclocondensation of 2-aminoarylmethanols with nitriles in air</a></h4>
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Green Chemistry</h3>
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Synthesis of 2-substituted quinazolines by CsOH-mediated direct aerobic oxidative cyclocondensation of 2-aminoarylmethanols with nitriles in air</h2>
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<span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3ASong%20Yao" style="color: #2d7ea9;">Song Yao</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span><span style="position: relative; top: -0.4em; vertical-align: baseline;">b</span> </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AKaijing%20Zhou" style="color: #2d7ea9;">Kaijing Zhou</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">b</span> </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AJiabing%20Wang" style="color: #2d7ea9;">Jiabing Wang</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span> </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AHongen%20Cao" style="color: #2d7ea9;">Hongen Cao</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">c</span> </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3ALei%20Yu" style="color: #2d7ea9;">Lei Yu</a>,<span style="position: relative; top: -0.4em; vertical-align: baseline;">c</span> </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AJianzhang%20Wu" style="color: #2d7ea9;">Jianzhang Wu</a>,<span style="font-size: 16px;">*</span><span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span> </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3APeihong%20Qiu" style="color: #2d7ea9;">Peihong Qiu</a><span style="font-size: 16px;">*</span><span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span> and </span><span class="article__author-link" style="font-size: 14px; line-height: 20px;"><a href="http://pubs.rsc.org/en/results?searchtext=Author%3AQing%20Xu" style="color: #2d7ea9;">Qing Xu</a><span style="font-size: 16px;">*</span><span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span><span style="position: relative; top: -0.4em; vertical-align: baseline;">b</span><span style="position: relative; top: -0.4em; vertical-align: baseline;">c</span> </span></div>
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<span style="display: table-cell; padding-left: 4px; width: 7px;">*</span><span style="display: table-cell; padding-left: 12px;">Corresponding authors</span></div>
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<span style="display: table-cell; padding-left: 4px; width: 7px;"><span style="position: relative; top: -0.4em; vertical-align: baseline;">a</span></span><span style="display: table-cell; padding-left: 12px;">Chemical Biology Research Center, College of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, China<br /><b>E-mail:</b> <a href="mailto:wjzwzmu@163.com" style="color: #9d3d99;" title="wjzwzmu@163.com">wjzwzmu@163.com</a>, <a href="mailto:wzqph@163.com" style="color: #9d3d99;" title="wzqph@163.com">wzqph@163.com</a><br /><b>Tel:</b> +86-158-25672558</span></div>
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<span style="display: table-cell; padding-left: 4px; width: 8px;"><span style="position: relative; top: -0.4em; vertical-align: baseline;">b</span></span><span style="display: table-cell; padding-left: 12px;">College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, P. R. China<br /><b>E-mail:</b> <a href="mailto:qing-xu@wzu.edu.cn" style="color: #9d3d99;" title="qing-xu@wzu.edu.cn">qing-xu@wzu.edu.cn</a><br /><b>Fax:</b> +86-577-86689302<br /><b>Tel:</b> +86-138-57745327</span></div>
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<span style="display: table-cell; padding-left: 4px; width: 7px;"><span style="position: relative; top: -0.4em; vertical-align: baseline;">c</span></span><span style="display: table-cell; padding-left: 12px;">Institute of Pesticide, School of Horticulture and Plant Protection and School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, China</span></div>
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By using air as the superior oxidant, a highly atom-efficient synthesis of 2-substituted quinazolines is developed by a CsOH-mediated direct aerobic oxidative reaction of the readily available and stable 2-aminoarylmethanols and nitriles. Effectively working as the promoter in the alcohol oxidation, nitrile hydration, and cyclocondensation steps, CsOH is the best base for the reaction. A similar method can also be extended to the synthesis of substituted quinolines starting from methyl ketones instead of nitriles.</div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-67308579413800688672017-05-15T17:41:00.002+05:302017-05-15T17:49:11.964+05:30USA Viewership touched 3 lakhs on New Drug Approvals<div dir="ltr" style="text-align: left;" trbidi="on">
<div style="background-color: white; color: #333333; font-family: Helvetica, Arial, Tahoma, sans-serif; font-size: 12px; margin-bottom: 10px;">
<img alt="str0" class="alignnone wp-image-21011" data-attachment-id="21011" data-comments-opened="1" data-image-description="" data-image-meta="{"aperture":"0","credit":"","camera":"","caption":"","created_timestamp":"0","copyright":"","focal_length":"0","iso":"0","shutter_speed":"0","title":"","orientation":"0"}" data-image-title="str0" data-large-file="https://newdrugapprovals.files.wordpress.com/2017/05/str0.png?w=289&h=339?w=186" data-medium-file="https://newdrugapprovals.files.wordpress.com/2017/05/str0.png?w=289&h=339?w=186" data-orig-file="https://newdrugapprovals.files.wordpress.com/2017/05/str0.png?w=289&h=339" data-orig-size="186,218" data-permalink="https://newdrugapprovals.org/2017/05/15/us-viewership-touched-3-lakhs-on-new-drug-approvals/str0-54/" height="339" sizes="(max-width: 289px) 100vw, 289px" src="https://newdrugapprovals.files.wordpress.com/2017/05/str0.png?w=289&h=339" srcset="https://newdrugapprovals.files.wordpress.com/2017/05/str0.png 186w, https://newdrugapprovals.files.wordpress.com/2017/05/str0.png?w=128&h=150 128w" style="border: 4px solid rgb(238, 238, 238); box-sizing: border-box; height: auto; max-width: 100%; vertical-align: middle;" width="289" /></div>
<div style="background-color: white; color: #333333; font-family: Helvetica, Arial, Tahoma, sans-serif; font-size: 12px; margin-bottom: 10px;">
USA Viewership touched 3 lakhs on New Drug Approvals</div>
<div style="background-color: white; color: #333333; font-family: Helvetica, Arial, Tahoma, sans-serif; font-size: 12px; margin-bottom: 10px;">
<a href="https://newdrugapprovals.org/" style="color: #0c5390; text-decoration-line: none;">https://newdrugapprovals.org/</a></div>
<div style="background-color: white; color: #333333; font-family: Helvetica, Arial, Tahoma, sans-serif; font-size: 12px; margin-bottom: 10px;">
Total 16.9 lakhs in 213 countries</div>
</div>
DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-10926489728414783752017-05-10T16:31:00.003+05:302017-05-10T16:31:37.546+05:30DR PRAVIN PATIL (Guest blogger) m-Chloroperbenzoic acid-oxchromium (VI)-mediated cleavage of 2,4,5-trisubstituted oxazoles <div dir="ltr" style="text-align: left;" trbidi="on">
<div style="background-color: white; color: #222222; font-family: arial, sans-serif; font-size: 12.8px;">
Here is the another publication details </div>
<div style="background-color: white; color: #222222; font-family: arial, sans-serif; font-size: 12.8px;">
<span style="font-size: 12.8px;">The paper is about m-CPBA/Chromium-VI mediated oxidation of oxazoles and published in Tetrahedron Letters recently.</span></div>
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<div class="ElsArticleTitle">
<b><i><span style="font-size: 11.0pt;">m</span></i></b><b><span style="font-size: 11.0pt;">-Chloroperbenzoic
acid-oxchromium (VI)-mediated cleavage of
2,4,5-trisubstituted oxazoles <o:p></o:p></span></b></div>
<div align="left" class="BBAuthorName">
<span style="font-size: 11.0pt;">Pravin C. Patil and Frederick A. Luzzio*<o:p></o:p></span></div>
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<span style="font-size: 11.0pt;">Department of Chemistry,
University of Louisville, 2320 South Brook Street, Louisville, Kentucky 40292
USA<o:p></o:p></span></div>
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<span style="background: yellow; font-size: 11pt;">[Invited article: Tetrahedron Letters <b>2017</b>, </span><span style="background: yellow; font-size: 11.0pt; mso-highlight: yellow;">58</span><span style="background: yellow; font-size: 11pt;"> (13),
1280-1282]</span><span style="font-size: 11pt;"><o:p></o:p></span></div>
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<span style="color: #0070c0; font-size: 11pt;"><a href="http://www.sciencedirect.com/science/article/pii/S004040391730196X"><span style="color: #0070c0;">http://www.sciencedirect.com/science/article/pii/S004040391730196X</span></a><o:p></o:p></span></div>
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<span style="color: #0070c0; font-size: 11pt;">DOI: <a href="https://doi.org/10.1016/j.tetlet.2017.02.027" target="doilink"><span style="background: white; border: none windowtext 1.0pt; color: #0070c0; mso-border-alt: none windowtext 0in; padding: 0in;">https://doi.org/10.1016/j.tetlet.2017.02.027</span></a>]<o:p></o:p></span></div>
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<b><span style="font-size: 11pt;">Graphical Abstract:<o:p></o:p></span></b></div>
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<b><span style="font-family: "Times New Roman","serif";">Abstract: <o:p></o:p></span></b></div>
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<span style="font-family: "Times New Roman","serif";">An
array of 2-substituted-4,5-diphenyloxazoles were found to be cleaved to
triacylamines and diacylamines (imides) using a reagent system composed of
3-chloroperbenzoic acid (MCPBA) and 2,2'-bipyridinium chlorochromate (BPCC).
The 2-alkyl-4,5-diphenyloxazoles give imides (38-60%) as the predominant
cleavage product while the 2-aryl-4,5-diphenyloxazoles give triacylamines
(62-71%). Two mechanisms involving intermediates such as cyclic endoperoxides
or oxachromacycles were proposed. An application of the oxidative cleavage to
the multi-step synthesis of phoracantholide I <i>seco</i> acid is detailed.<o:p></o:p></span></div>
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<span style="font-family: "Times New Roman","serif";">Application
of methodology toward synthesis of Phoracantholide-I <i>seco</i> acid<o:p></o:p></span></div>
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<span style="background-color: yellow;"><o:p> High</o:p><span style="font-size: 11pt;">lights</span></span></div>
<div class="MsoListParagraphCxSpFirst" style="line-height: normal; margin-bottom: .0001pt; margin-bottom: 0in; mso-add-space: auto; vertical-align: baseline;">
<span style="color: #2e2e2e; font-family: "Times New Roman","serif"; mso-fareast-font-family: "Times New Roman";">A new method for the cleavage of 2,4,5-trisubstituted oxazoles
to imides and triacylamines is detailed.<o:p></o:p></span></div>
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<span style="color: #2e2e2e; font-family: "Times New Roman","serif"; mso-fareast-font-family: "Times New Roman";">The oxidation system utilizes two reagents composed of a
peroxide and oxochromium (VI).<o:p></o:p></span></div>
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<span style="color: #2e2e2e; font-family: "Times New Roman","serif"; mso-fareast-font-family: "Times New Roman";">Mechanisms are proposed for the oxidative cleavage reaction.<o:p></o:p></span></div>
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<span style="color: #2e2e2e; font-family: "Times New Roman","serif"; mso-fareast-font-family: "Times New Roman";">A synthesis of (±)-phoracantholide <i><span style="border: none windowtext 1.0pt; mso-border-alt: none windowtext 0in; padding: 0in;">seco</span></i>-acid is detailed.<o:p></o:p></span></div>
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Dr. Pravin C. Patil</h1>
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see…….<a href="http://oneorganichemistoneday.blogspot.in/2017/04/dr-pravin-patil.html" style="border: 0px; color: #227ad1; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px; text-decoration-line: none;" target="_blank">http://oneorganichemistoneday.blogspot.in/2017/04/dr-pravin-patil.html</a></div>
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Dr. Pravin C Patil completed his B.Sc. (Chemistry) at ASC College Chopda (Jalgaon, Maharashtra, India) in 2001 and M.Sc. (Organic Chemistry) at SSVPS’S Science College Dhule in North Maharashtra University (Jalgaon, Maharashtra, India) in year 2003. After M.Sc. degree he was accepted for summer internship training program at Bhabha Atomic Research Center (BARC, Mumbai) in the laboratory of Prof. Subrata Chattopadhyay in Bio-organic Division. In 2003, Dr. Pravin joined to API Pharmaceutical bulk drug company, RPG Life Science (Navi Mumbai, Maharashtra, India) and worked there for two years. In 2005, he enrolled into Ph.D. (Chemistry) program at Institute of Chemical Technology (ICT), Matunga, Mumbai, aharashtra, under the supervision of Prof. K. G. Akamanchi in the department of Pharmaceutical Sciences and Technology.</div>
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After finishing Ph.D. in 2010, he joined to Pune (Maharashtra, India) based pharmaceutical industry, Lupin Research Park (LRP) in the department of process development. After spending two years at Lupin as a Research Scientist, he got an opportunity in June 2012 to pursue Postdoctoral studies at Hope College, Holland, MI, USA under the supervision of Prof. Moses Lee. During year 2012-13 he worked on total synthesis of achiral anticancer molecules Duocarmycin and its analogs. In 2014, he joined to Prof. Frederick Luzzio at the Department for Chemistry, University of Louisville, Louisville, KY, USA to pursue postdoctoral studies on NIH sponsored project “ Structure based design and synthesis of Peptidomimetics targeting P. gingivalis.</div>
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During his research experience, he has authored 23 international publications in peer reviewed journals and inventor for 4 patents.</div>
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//////////////<strong style="border: 0px; font-size: 13.92px; margin: 0px; outline: 0px; padding: 0px;">guest blogger, pravin patil</strong></div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-11489904461451256352017-04-29T18:22:00.001+05:302017-04-29T18:22:15.418+05:30Visible-light-induced and iron-catalyzed methylation of N-arylacrylamides with dimethyl sulphoxide: a convenient access to 3-ethyl-3-methyl oxindoles<div dir="ltr" style="text-align: left;" trbidi="on">
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<a data-mce-href="http://feeds.rsc.org/~r/rss/OB/~3/3oHToXV8mho/C7OB00779E" href="http://feeds.rsc.org/~r/rss/OB/~3/3oHToXV8mho/C7OB00779E" style="color: #222222;"><img align="center" data-mce-src="http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=C7OB00779E" src="http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=C7OB00779E" style="height: auto; margin-bottom: 10px; margin-top: 8px; max-width: 100%;" /></a></div>
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<a data-mce-href="http://feeds.rsc.org/~r/rss/OB/~3/3oHToXV8mho/C7OB00779E" href="http://feeds.rsc.org/~r/rss/OB/~3/3oHToXV8mho/C7OB00779E" style="color: #222222; text-decoration-line: none;">Visible-light-induced and iron-catalyzed methylation of N-arylacrylamides with dimethyl sulphoxide: a convenient access to 3-ethyl-3-methyl oxindoles</a></h4>
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<i><b>Org. Biomol. Chem.</b></i>, 2017, Advance Article<br /><b>DOI</b>: 10.1039/C7OB00779E, Paper</div>
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Zuguang Xie, Pinhua Li, Yu Hu, Ning Xu, Lei Wang<br />An efficient synthesis of 3-ethyl-3-methyl oxindoles by visible-light promoted and iron-catalyzed difunctionalization of <em>N</em>-arylacrylamides with dimethyl sulphoxide was developed</div>
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Visible-light-induced and iron-catalyzed methylation of <em>N</em>-arylacrylamides with dimethyl sulphoxide: a convenient access to 3-ethyl-3-methyl oxindoles</h2>
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<span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AZuguang%20Xie" href="http://pubs.rsc.org/en/results?searchtext=Author%3AZuguang%20Xie" style="color: #222222;">Zuguang Xie</a>,<span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">a</span> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3APinhua%20Li" href="http://pubs.rsc.org/en/results?searchtext=Author%3APinhua%20Li" style="color: #222222;">Pinhua Li</a>,*<span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">a</span> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3AYu%20Hu" href="http://pubs.rsc.org/en/results?searchtext=Author%3AYu%20Hu" style="color: #222222;">Yu Hu</a>,<span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">a</span> </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3ANing%20Xu" href="http://pubs.rsc.org/en/results?searchtext=Author%3ANing%20Xu" style="color: #222222;">Ning Xu</a><span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">a</span> and </span><span class="article__author-link"><a data-mce-href="http://pubs.rsc.org/en/results?searchtext=Author%3ALei%20Wang" href="http://pubs.rsc.org/en/results?searchtext=Author%3ALei%20Wang" style="color: #222222;">Lei Wang</a>*<span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">a</span><span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">b</span> </span></div>
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<a class="drawer__handle" data-mce-href="http://pubs.rsc.org/en/Content/ArticleLanding/2017/OB/C7OB00779E?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FOB+%28RSC+-+Org.+Biomol.+Chem.+latest+articles%29#" href="http://pubs.rsc.org/en/Content/ArticleLanding/2017/OB/C7OB00779E?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FOB+%28RSC+-+Org.+Biomol.+Chem.+latest+articles%29#" style="color: #222222;">Author affiliations</a></div>
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*Corresponding authors</div>
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<span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">a</span>Department of Chemistry, Huaibei Normal University, Huaibei, P. R. China<br /><b>E-mail:</b> <a data-mce-href="mailto:pphuali@126.com" href="mailto:pphuali@126.com" style="color: #222222;" title="pphuali@126.com">pphuali@126.com</a>, <a data-mce-href="mailto:leiwang@chnu.edu.cn" href="mailto:leiwang@chnu.edu.cn" style="color: #222222;" title="leiwang@chnu.edu.cn">leiwang@chnu.edu.cn</a><br /><b>Fax:</b> +86-561-3090-518<br /><b>Tel:</b> +86-561-3802-069</div>
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<span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">b</span>State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China</div>
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Abstract</h3>
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A visible-light-induced and iron-catalyzed methylation of arylacrylamides by dimethyl sulphoxide (DMSO) is achieved, leading to 3-ethyl-3-methyl indolin-2-ones in high yields. This reaction tolerates a series of functional groups, such as methoxy, trifluoromethyl, cyano, nitro, acetyl and ethyloxy carbonyl groups. The visible-light promoted radical methylation and arylation of the alkenyl group are involved in this reaction.</div>
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<img alt="Graphical abstract: Visible-light-induced and iron-catalyzed methylation of N-arylacrylamides with dimethyl sulphoxide: a convenient access to 3-ethyl-3-methyl oxindoles" data-mce-src="http://pubs.rsc.org/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=C7OB00779E" src="http://pubs.rsc.org/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=C7OB00779E" style="height: auto; margin-bottom: 10px; margin-top: 8px; max-width: 100%;" title="Graphical abstract" /></div>
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<a data-mce-href="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR1-46.jpg" href="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR1-46.jpg" style="color: #222222;"><img alt="str1" class="alignnone size-medium wp-image-3058" data-mce-src="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR1-46-300x205.jpg" height="205" src="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR1-46-300x205.jpg" style="height: auto; margin-bottom: 10px; margin-top: 8px; max-width: 100%;" width="300" /></a> <a data-mce-href="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR2-22.jpg" href="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR2-22.jpg" style="color: #222222;"><img alt="str2" class="alignnone size-medium wp-image-3059" data-mce-src="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR2-22-300x202.jpg" height="202" src="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR2-22-300x202.jpg" style="height: auto; margin-bottom: 10px; margin-top: 8px; max-width: 100%;" width="300" /></a></div>
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<a data-mce-href="http://www.rsc.org/suppdata/c7/ob/c7ob00779e/c7ob00779e1.pdf" href="http://www.rsc.org/suppdata/c7/ob/c7ob00779e/c7ob00779e1.pdf" style="color: #222222;">////</a>//</div>
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DRUG PATENTS INTERNATIONALhttp://www.blogger.com/profile/12652768774396889936noreply@blogger.com0tag:blogger.com,1999:blog-5314038650812093645.post-76796731452711673592017-04-29T18:19:00.001+05:302017-04-29T18:19:06.595+05:30N-Methyl-3-Bromo-5-Methyl Pyrazole<div dir="ltr" style="text-align: left;" trbidi="on">
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<span class="hlFld-Title"><i>N</i>-Methyl-3-Bromo-5-Methyl Pyrazole</span></h1>
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<b>3</b>·HCl as a white solid in 27% yield; sublimes at 40 °C; <span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">1</span>H NMR (500 MHz, DMSO-<i>d</i><span style="font-size: 12px; height: 0px; line-height: 0; position: relative; top: 0.5ex; vertical-align: baseline;">6</span>) δ 11.88 (s, 1 H), 6.07 (s, 1 H), 3.62 (s, 3 H), 2.16 (s, 3 H); <span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">13</span>C NMR (125 MHz, DMSO-<i>d</i><span style="font-size: 12px; height: 0px; line-height: 0; position: relative; top: 0.5ex; vertical-align: baseline;">6</span>) δ 141.7, 123.0, 107.5, 36.5, 10.9; HRMS-ESI (<i>m</i>/<i>z</i>) calcd for C<span style="font-size: 12px; height: 0px; line-height: 0; position: relative; top: 0.5ex; vertical-align: baseline;">5</span>H<span style="font-size: 12px; height: 0px; line-height: 0; position: relative; top: 0.5ex; vertical-align: baseline;">8</span>N<span style="font-size: 12px; height: 0px; line-height: 0; position: relative; top: 0.5ex; vertical-align: baseline;">2</span>Br [M + H]<span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">+</span> 174.9864, found 174.9864.</div>
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<b>3</b>·TfOH as an off-white solid; mp = 145 °C; <span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">1</span>H NMR (400 MHz, DMSO-<i>d</i><span style="font-size: 12px; height: 0px; line-height: 0; position: relative; top: 0.5ex; vertical-align: baseline;">6</span>) δ 11.73 (s, 1 H), 6.06 (s, 1 H), 3.62 (s, 3 H), 2.16 (s, 3 H); <span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">13</span>C NMR (100 MHz, DMSO-<i>d</i><span style="font-size: 12px; height: 0px; line-height: 0; position: relative; top: 0.5ex; vertical-align: baseline;">6</span>) δ 141.9, 123.2, 121.2 (q, <i>J</i> = 320 Hz), 107.6, 36.5, 10.9; HRMS-ESI (<i>m</i>/<i>z</i>) calcd for C<span style="font-size: 12px; height: 0px; line-height: 0; position: relative; top: 0.5ex; vertical-align: baseline;">5</span>H<span style="font-size: 12px; height: 0px; line-height: 0; position: relative; top: 0.5ex; vertical-align: baseline;">8</span>N<span style="font-size: 12px; height: 0px; line-height: 0; position: relative; top: 0.5ex; vertical-align: baseline;">2</span>Br [M + H]<span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">+</span> 174.9864, found 174.9865.</div>
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<span class="hlFld-Title">Development of Scalable Processes for the Preparation of <i>N</i>-Methyl-3-Bromo-5-Methyl Pyrazole</span></h1>
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<div id="authors">
<span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Fox%2C+Richard+J" href="http://pubs.acs.org/author/Fox%2C+Richard+J" id="authors" style="color: #222222;">Richard J. Fox</a><a class="ref" data-mce-href="http://pubs.acs.org/doi/full/10.1021/acs.oprd.7b00091#cor1" href="http://pubs.acs.org/doi/full/10.1021/acs.oprd.7b00091#cor1" style="color: #222222;"><span style="bottom: 1ex; font-size: 12px; height: 0px; line-height: 0; position: relative; vertical-align: baseline;">*</span></a><span class="orcid-link-icon"> <a data-mce-href="http://orcid.org/0000-0003-1117-7963" href="http://orcid.org/0000-0003-1117-7963" style="color: #222222;" target="_blank"><img data-mce-src="http://pubs.acs.org/templates/jsp/images/orcid.png" src="http://pubs.acs.org/templates/jsp/images/orcid.png" style="height: auto; margin-bottom: 10px; margin-top: 8px; max-width: 100%;" /></a></span>, </span><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Markwalter%2C+Chester+E" href="http://pubs.acs.org/author/Markwalter%2C+Chester+E" id="authors" style="color: #222222;">Chester E. Markwalter</a>, </span><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Lawler%2C+Michael" href="http://pubs.acs.org/author/Lawler%2C+Michael" id="authors" style="color: #222222;">Michael Lawler</a>, </span><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Zhu%2C+Keming" href="http://pubs.acs.org/author/Zhu%2C+Keming" id="authors" style="color: #222222;">Keming Zhu</a>, </span><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Albrecht%2C+Jacob" href="http://pubs.acs.org/author/Albrecht%2C+Jacob" id="authors" style="color: #222222;">Jacob Albrecht</a>, </span><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Payack%2C+Joseph" href="http://pubs.acs.org/author/Payack%2C+Joseph" id="authors" style="color: #222222;">Joseph Payack</a>, and </span><span class="hlFld-ContribAuthor"><a data-mce-href="http://pubs.acs.org/author/Eastgate%2C+Martin+D" href="http://pubs.acs.org/author/Eastgate%2C+Martin+D" id="authors" style="color: #222222;">Martin D. Eastgate</a></span></div>
<div class="affiliations">
<div id="aff1">
Chemical & Synthetic Development, <span class="institution">Bristol-Myers Squibb Company</span>, P.O. Box 191 New Brunswick, New Jersey 08903-0191, <span class="country">United States</span></div>
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<div id="citation">
<cite>Org. Process Res. Dev.</cite>, Article ASAP</div>
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<strong>DOI: </strong>10.1021/acs.oprd.7b00091</div>
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*E-mail: <a data-mce-href="mailto:richard.fox@bms.com" href="mailto:richard.fox@bms.com" style="color: #222222;">richard.fox@bms.com</a>.</div>
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<a class="showFiguresEvent" data-mce-href="http://pubs.acs.org/doi/full/10.1021/acs.oprd.7b00091#" href="http://pubs.acs.org/doi/full/10.1021/acs.oprd.7b00091#" id="absImg" style="color: #222222;" title="Open Figure Viewer"><img alt="Abstract Image" data-mce-src="http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/oprdfk/0/oprdfk.ahead-of-print/acs.oprd.7b00091/20170426/images/medium/op-2017-00091x_0014.gif" src="http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/oprdfk/0/oprdfk.ahead-of-print/acs.oprd.7b00091/20170426/images/medium/op-2017-00091x_0014.gif" style="height: auto; margin-bottom: 10px; margin-top: 8px; max-width: 100%;" /></a></div>
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The development and optimization of two scalable routes to <i>N-</i>methyl-3-bromo-5-methyl pyrazole is described. The initial Sandmeyer route entailed a three-step sequence from crotonitrile and methyl hydrazine, proceeding through the 3-amino pyrazole intermediate. Due to the GTI liability of the 3-amino pyrazole intermediate, a tedious steam-distillation, and <30% overall yield, we developed a second-generation Sandmeyer-free approach from methyl crotonate and methyl hydrazine which leveraged a condensation, bromination, and oxidation sequence. Process development led to the improved preparation of <i>N-</i>methyl-3-bromo-5-methyl pyrazole with increased efficiency and overall yield. The isolation, handling, and storage of the final product was greatly improved through the generation of the triflic acid salt, and salt form studies are also discussed.</div>
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<a data-mce-href="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR1-49.jpg" href="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR1-49.jpg" style="color: #222222;"><img alt="str1" class="alignnone size-medium wp-image-3088" data-mce-src="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR1-49-300x202.jpg" height="202" src="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR1-49-300x202.jpg" style="height: auto; margin-bottom: 10px; margin-top: 8px; max-width: 100%;" width="300" /></a> <a data-mce-href="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR2-24.jpg" href="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR2-24.jpg" style="color: #222222;"><img alt="str2" class="alignnone size-medium wp-image-3089" data-mce-src="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR2-24-300x199.jpg" height="199" src="http://drugapprovalsint.com/wp-content/uploads/2017/04/STR2-24-300x199.jpg" style="height: auto; margin-bottom: 10px; margin-top: 8px; max-width: 100%;" width="300" /></a> <a data-mce-href="http://drugapprovalsint.com/wp-content/uploads/2017/04/str3-3.jpg" href="http://drugapprovalsint.com/wp-content/uploads/2017/04/str3-3.jpg" style="color: #222222;"><img alt="str3" class="alignnone size-medium wp-image-3090" data-mce-src="http://drugapprovalsint.com/wp-content/uploads/2017/04/str3-3-300x192.jpg" height="192" src="http://drugapprovalsint.com/wp-content/uploads/2017/04/str3-3-300x192.jpg" style="height: auto; margin-bottom: 10px; margin-top: 8px; max-width: 100%;" width="300" /></a> <a data-mce-href="http://drugapprovalsint.com/wp-content/uploads/2017/04/str4-6.jpg" href="http://drugapprovalsint.com/wp-content/uploads/2017/04/str4-6.jpg" style="color: #222222;"><img alt="str4" class="alignnone size-medium wp-image-3091" data-mce-src="http://drugapprovalsint.com/wp-content/uploads/2017/04/str4-6-300x200.jpg" height="200" src="http://drugapprovalsint.com/wp-content/uploads/2017/04/str4-6-300x200.jpg" style="height: auto; margin-bottom: 10px; margin-top: 8px; max-width: 100%;" width="300" /></a></div>
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<cite>Org. Process Res. Dev.</cite>, Article ASAP</div>
<div id="doi" style="color: #222222; font-family: "Open Sans", Tahoma, Verdana, Segoe, sans-serif; font-size: 16px;">
<strong>DOI: </strong>10.1021/acs.oprd.7b00091</div>
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<a data-mce-href="http://pubs.acs.org/doi/suppl/10.1021/acs.oprd.7b00091/suppl_file/op7b00091_si_001.pdf" href="http://pubs.acs.org/doi/suppl/10.1021/acs.oprd.7b00091/suppl_file/op7b00091_si_001.pdf" style="color: #222222;">///////</a>//////</div>
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