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Ruthenium(II)-Catalyzed Regioselective C–H Arylation of Cyclic and N,N-Dialkyl Benzamides with Boronic Acids by Weak Coordination

Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States
ACS Catal., 2016, 6 (7), pp 4755–4759
DOI: 10.1021/acscatal.6b01360
Publication Date (Web): June 22, 2016
Copyright © 2016 American Chemical Society

Abstract

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We disclose a general method for selective ortho-C–H arylation of cyclic and N,N-dialkyl benzamides with boronic acids enabled by versatile ruthenium(II) complexes. This method features a general C–H arylation of ubiquitous aromatic tertiary benzamides by weak O-coordination. The transformation is characterized by its operational simplicity, the use of inexpensive, air-stable Ru(II) catalysts, scalability, and wide substrate scope. The reaction proceeds with high monoarylation selectivity to furnish valuable tertiary amide biaryls. Most crucially, the method provides the long-sought alternative to the classic directed-ortho-metalation (DoM) strategy, obviating the need for cryogenic conditions and strong lithium bases.

Keywords: 

amides; boronic acids; C−H activation; directed-ortho-metalation; ruthenium





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