Practical Synthesis of Amides via Copper/ABNO-Catalyzed Aerobic Oxidative Coupling of Alcohols and Amines

J Am Chem Soc. 2016 May 25;138(20):6416-9. doi: 10.1021/jacs.6b03931. Epub 2016 May 16.

Abstract

A modular Cu/ABNO catalyst system has been identified that enables efficient aerobic oxidative coupling of alcohols and amines to amides. All four permutations of benzylic/aliphatic alcohols and primary/secondary amines are viable in this reaction, enabling broad access to secondary and tertiary amides. The reactions exhibit excellent functional group compatibility and are complete within 30 min-3 h at rt. All components of the catalyst system are commercially available.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aerobiosis
  • Alcohols / chemistry*
  • Amides / chemical synthesis*
  • Amines / chemistry*
  • Copper / chemistry*
  • Oxidation-Reduction
  • Oxygen / chemistry*

Substances

  • Alcohols
  • Amides
  • Amines
  • Copper
  • Oxygen