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Letter

Copper-Catalyzed Amidation of Allylic and Benzylic CH Bonds

Supporting Info

Guillaume Pelletier and David A. Powell*

Merck Frosst Centre for Therapeutic Research, 16711 Trans Canada Highway, Kirkland, Qubec H9H 3L1, Canada

Org. Lett., 2006, 8 (26), pp 6031–6034

DOI: 10.1021/ol062514u

Publication Date (Web): November 18, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, david_powell2@merck.com

Abstract

A copper-catalyzed amidation of allylic and benzylic C−H bonds with both primary and secondary sulfonamides is described. The reaction is applicable to the coupling of a diverse set of hydrocarbon species with aryl, heteroaryl, and alkyl sulfonamides and is tolerant of a variety of functional groups. Mechanistic insight has been gained through the isolation of a benzylic acetate intermediate, which was demonstrated to undergo facile conversion to the substituted sulfonamide product under copper catalysis.

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History

Published In Issue December 21, 2006
Received October 11, 2006

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Letter

Copper-Catalyzed Amidation of Allylic and Benzylic CH Bonds