A general metal free approach to α-ketoamides via oxidative amidation-diketonization of terminal alkynes

Chem Commun (Camb). 2014 Aug 28;50(67):9533-5. doi: 10.1039/c4cc03783a.

Abstract

A novel catalytic system TMSOTf/I2/DMSO for the oxidative coupling of terminal alkynes with virtually any primary/secondary amine leading to α-ketoamides has been developed. The reaction possibly proceeds via iminium ion formation, wherein DMSO acts as a solvent as well as an oxidizing agent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Amides / chemistry*
  • Catalysis
  • Dimethyl Sulfoxide / chemistry
  • Iodine / chemistry
  • Ketones / chemistry*
  • Mesylates / chemistry
  • Oxidative Coupling*
  • Trimethylsilyl Compounds / chemistry

Substances

  • Alkynes
  • Amides
  • Ketones
  • Mesylates
  • Trimethylsilyl Compounds
  • trimethylsilyl trifluoromethanesulfonate
  • Iodine
  • Dimethyl Sulfoxide