Imine Reduction Using Iron Catalysts

Imine Reduction Using Iron Catalysts

Abnormal-NHC-Fe(0) complex outperforms noble metal catalysts


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http://www.chemistryviews.org/details/news/9749451/Imine_Reduction_Using_Iron_Catalysts.html?elq_mid=11741&elq_cid=1558306

A Highly Efficient Base-Metal Catalyst: Chemoselective Reduction of Imines to Amines Using An Abnormal-NHC–Fe(0) Complex

Mrinal Bhunia†, Pradip Kumar Hota†, Gonela Vijaykumar†, Debashis Adhikari‡, and Swadhin K. Mandal*†

† Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur 741246, India

‡ Department of Chemical Sciences, Indian Institute of Science Education and Research Mohali, SAS Nagar 140306, India

Organometallics, Article ASAP

DOI: 10.1021/acs.organomet.6b00478

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*E-mail for S.K.M.: swadhin.mandal@iiserkol.ac.in.

http://pubs.acs.org/doi/abs/10.1021/acs.organomet.6b00478

A base-metal, Fe(0)-catalyzed hydrosilylation of imines to obtain amines is reported here which outperforms its noble-metal congeners with the highest TON of 17000. The catalyst, (aNHC)Fe(CO)4, works under very mild conditions, with extremely low catalyst loading (down to 0.005 mol %), and exhibits excellent chemoselectivity. The facile nature of the imine reduction under mild conditions has been further demonstrated by reducing imines towards expensive commercial amines and biologically important N-alkylated sugars, which are difficult to achieve otherwise. A mechanistic pathway and the source of chemoselectivity for imine hydrosilylation have been proposed on the basis of the well-defined catalyst and isolable intermediates along the catalytic cycle.



Swadhin K. Mandal

Swadhin Mandal Associate Professor Dept: Chemical Sciences (DCS) E-mail: swadhin.mandal [at] iiserkol.ac.in Personal homepage: Click Here

Research Interest: 

Organometallic chemistry and its application in catalysis, new drug development and material chemistry

Academic Background:

1. BSc (Chemistry), University of Kalyani, 1993, Secured 3rd Rank in University
2. MSc (Chemistry), University of Kalyani, 1996, Secured first rank in University
3. PhD (Chemistry), Indian Institute of Science Bangalore, 2002

Positions:

1. Postdoctoral Fellow, University of California, Riverside (2002 - 2005)
2. Alexander von Humboldt Fellow, University of Goettingen (2006 - 2007)
3. Assistant Professor, IISER Kolkata (2007 - 2013)
4. Associate Professor, IISER Kolkata (2013 - 2014)
5. Associate Professor, IISER Kolkata ( - )

Awards and Honors:

1. Alexander von Humboldt Fellowship from Alexander von Humboldt Foundation (2005)
2. YIM Boston Young Scientist Award from YIM Boston at MIT, USA (2012)

Selected Publications
    

• Bhunia et al. Organometallics, in press, 2016. ​
• Paira, Singh et al. J. Org. Chem., 2016, 81 (6), 2432-2441.

• Pariyar et al.  J. Am. Chem. Soc. 2015, 137, 5955-5960 (This work was highlighted by Press coverage, see some links  natureINDIA, Business Standard, IBN7, The Statesman,ZeeNews, Yahoo, Crazyengineers, Delhi Daily News, India Samvad, Kansas City Post,Indianapolis Post,  Toronto Telegraph, Seattle India, Maine Mirror, Hawaii Telegraph,Indusage).
• Hota et al. Adv. Synth. Cat. 2015, 357, 3162 - 3170.
• Raha Roy et al.  ACS Catalysis 2014, 4, 4307–4319 (Selected as a significant recent publicationin a cross-journal virtual issue designed to showcase the significant recent publications among ACS Catalysis, Journal of the American Chemical Society, Journal of Organic Chemistry, and Organic Letters.)
• Raha Roy et al.  J. Org. Chem. 2014, 79, 9150-9160. 
•  Sau et al.  Chem. Asian J 2014, 9, 2806-2813. 
• Raman et al. Nature , 2013., 493, 509-513 ( This work was selected for Press Release coverage by Nature, see some links Telegraph, Deccan Herald, Nature India, please see Press Release for more news coverage on this work for further details)
• Santra et al. ACS Catalysis  2013, 3, 2776−2789.
• Mukherjee et al. Organometallics  2013, 32, 7213-7224
• Sau et al. Adv. Synth. Cat.  2013, 355, 2982-2991
• Mukherjee et al. Scientific Reports  2013, 3, 2821.
• Mukherjee et al. Chem. Eur. J. 2012, 18, 10530-10545 (Highlighted with  Frontispiece Graphics)
• Sen et al. Chem. Eur. J. 2012, 18, 54-58.
• Sau et al. Chem. Commun. 2012, 48, 555-557.
• Santra et al. Green Chem. 2011, 13, 3238 – 3247.
• Sen et al. Chem. Commun. 2011, 47, 11972–11974
• Mukherjee et al. Angew. Chem. Int. Ed. 2011, 50, 3968–3972  (Hot Paper)

Professional Recognitions

• "SKM delivers Physics Colloquium at University of Greifswald, Germany", 2016.
• Selected  and presented work as one of the six speakers in “Organometallics Fellowship Symposium” organized at San Francisco during 10-14th August, USA by the ACS Journal Organometallics.
• Joined Editorial Advisory Board of the Journal 'Organometallics' published by American Chemical Society 2013-2015
• Recipient of YIM-Young Scientist Award -2012 by YIM-Boston held during 6-8th October, 2012 at MIT, Boston, USA for his contribution in the area of Organometallic Chemistry. He is one of the two recipients of this award for the year 2012.
• Alexander von Humboldt Fellowship during 2006-2007 at University of Goettingen, Germany.

Selected Publications:

1. Raman, Karthik V; Kamerbeek, Alexander M.; Mukherjee, Arup; Atodiresei, Nicolae; Sen, Tamal K; Lazic, Predrag; Caciuc, Vasile; Michel, Reent; Stalke, Dietmar; Mandal, Swadhin K; Bluegel, Stephan; Muenzenberg, Markus and Moodera, Jagadeesh. 2013. "Interface-engineered templates for molecular spin memory devices." Nature, 493, 509-513
2. Sen, Tamal K; Mukherjee, Arup; Modak, Arghya; Mandal, Swadhin K and Koley, Debasis. 2013. "Substitution Effect on Phenalenyl Backbone in the Rate of Organozinc Catalyzed ROP of Cyclic Esters." Dalton Trans., 42, 1893-1904
3. Mukherjee, Arup; Sen, Tamal K.; Ghorai, Pradip Kr.; Samuel, Prinson P.; Schulzke, Carola and Mandal, Swadhin K. 2012. "Phenalenyl-Based Organozinc Catalysts for Intramolecular Hydroamination Reactions: A Combined Catalytic, Kinetic, and Mechanistic Investigation of the Catalytic Cycle." Chemistry -A European Journal, 18, 10530-545

Gonela Vijay Kumar, SRF
Research Interest:
Development of Nucleophilic Boron Compounds and its Reactivity.
Email - gonela.vijaykumar@gmail.com

Pradip Kumar Hota, SRF
Research Interest:
Transition Metal Mediated  C-C Coupling Reactions.
Email - pradip.hota87@gmail.com

Mrinal Bhunia, SRF
Research Interest:
Development of Abnormal Carbene based Transition Metal Complexes for Synthesis of Pharmaceutically Important Molecules.
Email - mrinalbhuniaa@gmail.com