Showing posts with label Directed Route to Biaryls. Show all posts

Tuesday, 6 September 2016

Directed Route to Biaryls

Directed Route to Biaryls

Palladium(II)-catalyzed C–H arylation of aromatic alcohols directed by quinolinyl acetal

Read more

http://www.chemistryviews.org/details/ezine/9692891/Directed_Route_to_Biaryls.html?elq_mid=11741&elq_cid=1558306

Previous article in issue: The Synthesis of trans-Flavan-3-ol Gallates by Regioselective Oxidative Etherification and Their Cytotoxicity Mediated by 67 LR
Next article in issue: Visible-Light-Induced Trifluoromethylation of Isonitrile-Substituted Methylenecyclopropanes: Facile Access to 6-(Trifluoromethyl)-7,8-Dihydrobenzo[k]phenanthridine Derivatives

View issue TOC
Volume 22, Issue 37
September 5, 2016
Pages 13054–13058

Palladium(II)-Catalyzed ortho-Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold

emferr@uga.edu

Department of Chemistry, University of Georgia, Athens, GA, USA

DOI: 10.1002/chem.201602844

Authors

hemiacetal 9 (0.811 g, Rf = 0.21 in 1:1 hexanes/EtOAc) as yellow solid. (Total amount: 6.87 g, 92% yield over 3 steps). Hemiacetal 9 (characterized as a 100:3 mixture of hemiacetal/aldehyde):

1 H NMR (400 MHz, DMSOd6) δ 8.31 (s, 1H), 8.06 (d, J = 8.5 Hz, 1H), 8.01 (d, J = 8.2 Hz, 1H), 7.81-7.72 (m, 1H), 7.66-7.58 (m, 1H), 7.09 (d, J = 7.6 Hz, 1H), 6.27 (d, J = 7.6 Hz, 1H), 5.25 (d, J = 13.6 Hz, 1H), 5.10 (dd, J = 13.6, 1.0 Hz, 1H);

13C NMR (100 MHz, DMSO-d6) δ 161.5, 147.7, 130.6, 129.3, 128.9, 128.2, 127.4, 126.7, 97.9, 68.3; IR (film) 3194, 1504, 1020, 910, 754 cm-1 ;

HRMS (ESI+) m/z calc’d for (M + H)+ [C11H9NO2 + H]+ : 188.0706, found 188.0706.

Image result for Prof. Dr. Eric M. Ferreira

Contact Information:

Associate Professor of Chemistry
University of Georgia
Chemistry Department
Athens, GA 30602
Tel. (706) 542-4231
emferr@uga.edu

As an undergraduate student at Massachusetts Institute of Technology (1996-2000), Eric worked on copper-catalyzed conjugate reduction chemistry under the direction of Professor Stephen Buchwald. His Ph.D. research with Professor Brian Stoltz at the California Institute of Technology (2000-2005) focused on the development of synthetically useful novel oxidation systems using palladium catalysis. Upon completion, he then continued his studies as an American Cancer Society postdoctoral associate at Stanford (2005-2008) with Prof. Barry Trost, where his studies concerned the use of ruthenium and palladium catalyzed cycloisomerizations for the formation of polycyclic compounds. He then began his independent career as an assistant professor at Colorado State University in 2008. Eric is currently an Associate Professor of Chemistry at the University of Georgia in Athens, GA.