Selective formation of secondary amides via the copper-catalyzed cross-coupling of alkylboronic acids with primary amides

Org Lett. 2013 May 3;15(9):2314-7. doi: 10.1021/ol401004r. Epub 2013 Apr 23.

Abstract

For the first time, a general catalytic procedure for the cross-coupling of primary amides and alkylboronic acids is demonstrated. The key to the success of this reaction was the identification of a mild base (NaOSiMe3) and oxidant (di-tert-butyl peroxide) to promote the copper-catalyzed reaction in high yield. This transformation provides a facile, high-yielding method for the monoalkylation of amides.

Publication types

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

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Boronic Acids / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Oxidants / chemistry*
  • Peroxides / chemistry*

Substances

  • Amides
  • Boronic Acids
  • Oxidants
  • Peroxides
  • di-tert-butyl peroxide
  • Copper