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Org Lett. 2006 Dec 21;8(26):6031-4.

Copper-catalyzed amidation of allylic and benzylic C-H bonds.

Author information

1
Merck Frosst Centre for Therapeutic Research, 16711 Trans Canada Highway, Kirkland, Qu├ębec H9H 3L1, Canada.

Abstract

[Structure: see text] 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.

PMID:
17165922
DOI:
10.1021/ol062514u
[Indexed for MEDLINE]

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