Novel and direct transformation of methyl ketones or carbinols to primary amides by employing aqueous ammonia

Org Lett. 2009 Sep 3;11(17):3810-3. doi: 10.1021/ol901250c.

Abstract

A novel and direct transformation of aryl, heteroaryl, vinyl, or ethynyl methyl ketones or carbinols to corresponding primary amides has been developed. An iodine-NH(3).H(2)O system was proven to be efficient for this reaction and afforded the expected products with good yields in aqueous media. A tandem Lieben-Haller-Bauer reaction mechanism was involved in this type of reaction and is proposed for the first time.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Ammonia / chemistry*
  • Catalysis
  • Iodine / chemistry
  • Ketones / chemistry*
  • Methanol / chemistry*
  • Molecular Structure
  • Water / chemistry

Substances

  • Amides
  • Ketones
  • Water
  • Ammonia
  • Iodine
  • Methanol