Cross-Coupling of Primary Amides to Aryl and Heteroaryl Partners Using (DiMeIHept^Cl)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

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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

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ID: J48-Y2017