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Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes

Richard Y. Liu, Minwoo Bae and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: sbuchwalmit.edu

R. Y. Liu, M. Bae, S. L. Buchwald, J. Am. Chem. Soc., 2018, 140, 1627-1631.

DOI: 10.1021/jacs.8b00643 (free Supporting Information)


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Abstract

A copper-hydride-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. The reaction avoids a typically challenging 1,2-siloxane elimination step, proceeds at ambient temperature, and tolerates a variety of metal-, acid-, or base-sensitive functional groups.

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proposed mechanism



Key Words

nitriles, silanes, CuH


ID: J48-Y2018