General and efficient copper-catalyzed amidation of saturated C-H bonds using N-halosuccinimides as the oxidants

J Org Chem. 2008 Aug 15;73(16):6207-12. doi: 10.1021/jo800624m. Epub 2008 Jul 2.

Abstract

We have developed a general and efficient method for copper-catalyzed amidation of saturated C-H bonds under mild conditions, and the used substrates include benzylic reagents, the N, N-dimethylaniline derivatives, the free carboxamides, and sulfonamides. The protocol uses inexpensive and readily available CuBr/ N-halosuccinimide (NBS or NCS) as the catalyst/oxidant, so it provides practical applications for synthesis of various amides via C-H activation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Benzyl Compounds / chemistry
  • Bromosuccinimide / chemistry
  • Catalysis
  • Copper / chemistry*
  • Oxidants / chemistry*
  • Succinimides / chemistry*

Substances

  • Amides
  • Benzyl Compounds
  • Oxidants
  • Succinimides
  • N-chlorosuccinimide
  • Copper
  • Bromosuccinimide