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

Org Lett. 2006 Dec 21;8(26):6031-4. doi: 10.1021/ol062514u.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Catalysis
  • Copper / chemistry*

Substances

  • Amides
  • Copper