Palladium-catalyzed C-H functionalization of N-arylpropiolamides with aryliodonium salts: selective synthesis of 3-(1-arylmethylene)oxindoles

J Org Chem. 2008 Jul 18;73(14):5476-80. doi: 10.1021/jo8008808. Epub 2008 Jun 17.

Abstract

A selective and efficient method for the synthesis of 3-(1-arylmethylene)oxindoles by palladium-catalyzed C-H functionalization of anilides with aryliodonium salts has been developed. In the presence of Pd(OAc)2 and Et3N, a variety of anilides underwent the reaction with aryliodonium salts to afford the corresponding 3-(1-arylmethylene)oxindoles in moderate to good yields. It is noteworthy that the reaction can be conducted providing moderate yields even without bases. The mechanism of the reaction was also discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Carbon / chemistry*
  • Catalysis
  • Hydrogen / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Iodine Compounds / chemistry*
  • Methane / chemistry*
  • Molecular Structure
  • Oxindoles
  • Palladium / chemistry*
  • Salts / chemistry

Substances

  • Amides
  • Indoles
  • Iodine Compounds
  • Oxindoles
  • Salts
  • 2-oxindole
  • Palladium
  • Carbon
  • Hydrogen
  • Methane