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Copper-Catalyzed Petasis-Type Reaction: A General Route to α-Substituted Amides From Imines, Acid Chlorides, and Organoboron Reagents

Marie S. T. Morin, Yingdong Lu, Daniel A. Black and Bruce A. Arndtsen*

*Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec H3A 2K6, Canada, Email: bruce.arndtsenmcgill.ca

M. S. T. Morin, Y. Lu, D. A. Black, B. A. Arndtsen, J. Org. Chem., 2012, 77, 2013-2017.

DOI: 10.1021/jo202339v (free Supporting Information)


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Abstract

A copper-catalyzed Petasis-type reaction of imines, acid chlorides, and organoboranes gives α-substituted amides. This reaction does not require the use of activated imines or the transfer of special units from the organoboranes and represent a useful generalization of the Petasis reaction.

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proposed intermediates



Key Words

Petasis Reaction, Arylation, Alkylation


ID: J42-Y2012-0390