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Cross-Coupling of Primary Amides to Aryl and Heteroaryl Partners Using (DiMeIHeptCl)Pd Promoted by Trialkylboranes or B(C6F5)3

Sepideh Sharif, Jonathan Day, Howard N. Hunter, Yu Lu, David Mitchell, Michael J. Rodriguez and Michael G. Organ*

*Department of Chemistry, York University 4700 Keele Street, Toronto M3J 1P3, Canada, Email: organuottawa.ca

S. Sharif, J. Day, H. N. Hunter, Y. Lu, D. Mitchell, M. J. Rodriguez, M. G. Organ, J. Am. Chem. Soc., 2017, 139, 18436-18439.

DOI: 10.1021/jacs.7b09488 (free Supporting Information)


Abstract

Boron-derived Lewis acids effectively promote the coupling of amide nucleophiles to various aryl and heteroaryl chlorides using a bulky Pd-NHC catalyst. It's proposed that boron-imidates form under the basic reaction conditions that aid coordination of nitrogen to Pd(II), which is rate limiting, and directly delivers the intermediate for reductive elimination.

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Key Words

amides


ID: J48-Y2017