Copper-catalyzed Petasis-type reaction: a general route to α-substituted amides from imines, acid chlorides, and organoboron reagents

J Org Chem. 2012 Feb 17;77(4):2013-7. doi: 10.1021/jo202339v. Epub 2012 Jan 30.

Abstract

A copper-catalyzed Petasis-type reaction of imines, acid chlorides, and organoboranes to form α-substituted amides is described. This reaction does not require the use of activated imines or the transfer of special units from the organoboranes and represent a useful generalization of the Petasis reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Benzoates / chemistry*
  • Boranes / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Imines / chemistry*
  • Lewis Bases / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Pyridines / chemistry

Substances

  • Amides
  • Benzoates
  • Boranes
  • Imines
  • Lewis Bases
  • Pyridines
  • Copper
  • 4-toluic acid
  • cuprous chloride
  • pyridine