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

Author(s)
Liu, Richard; Bae, Minwoo; Buchwald, Stephen Leffler
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Abstract
Metal-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. We report a copper-hydride(CuH)-catalyzed process that avoids a typically challenging 1,2-siloxane elimination step, thereby dramatically increasing the rate of the overall transformation relative to alternative metal-catalyzed systems. This new reaction proceeds at ambient temperature, tolerates a variety of metal-, acid-, or base-sensitive functional groups, and can be performed using a simple ligand, inexpensive siloxanes, and low catalyst loading. Keywords: Amides; Ligands; Nitrogen compounds; Dehydration; Chemical reactions
Date issued
2018-01-29
URI
https://hdl.handle.net/1721.1/125372
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Liu, Richard Y., Bae, Minwoo, and Buchwald, Stephen L. "Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes." Journal of the American Chemical Society 140, 5 (January 2018): 1627–1631 © 2018 American Chemical Society.
Version: Author's final manuscript
ISSN
0002-7863
1520-5126

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