Copper-catalyzed aerobic oxidative synthesis of α-ketoamides from methyl ketones, amines and NIS at room temperature

Org Biomol Chem. 2012 Dec 14;10(46):9237-42. doi: 10.1039/c2ob26586a. Epub 2012 Oct 26.

Abstract

A simple, efficient and practical copper-catalyzed aerobic oxidative synthesis of α-ketoamides from aryl methyl ketones, aliphatic amines and N-iodosuccinimide (NIS) has been developed. The one-pot reaction may proceed smoothly at room temperature in the open air. The possible mechanism for the formation of α-ketoamides was proposed. Molecular oxygen in air functions as both an oxidant and an oxygen source.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Air
  • Amides / chemical synthesis*
  • Amines / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Ketones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxidation-Reduction
  • Oxygen / chemistry*
  • Stereoisomerism
  • Succinimides / chemistry*
  • Temperature

Substances

  • Amides
  • Amines
  • Ketones
  • Succinimides
  • N-iodosuccinimide
  • Copper
  • Oxygen