Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 5, Pages 1627-1631Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b00643
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Funding
- National Institutes of Health [GM058160, GM122483, GM058160-17S1]
- MIT
- Bristol Myers Squibb
- Samsung Group
- MIT through the Undergraduate Research Opportunities Program
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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.
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