One-pot and regiospecific synthesis of 2,3-disubstituted indoles from 2-bromoanilides via consecutive palladium-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination

J Org Chem. 2013 May 3;78(9):4558-62. doi: 10.1021/jo302679f. Epub 2013 Apr 12.

Abstract

A practical one-pot and regiospecific three-component process for the synthesis of 2,3-disubstituted indoles from 2-bromoanilides was developed via consecutive palladium-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination.

MeSH terms

  • Amides / chemistry*
  • Anilides / chemistry*
  • Catalysis
  • Cyclization
  • Hydrocarbons, Brominated / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Oxidation-Reduction
  • Palladium / chemistry*

Substances

  • Amides
  • Anilides
  • Hydrocarbons, Brominated
  • Indoles
  • Organometallic Compounds
  • Palladium