Exploring the oxidative cyclization of substituted N-aryl enamines: Pd-catalyzed formation of indoles from anilines

Chemistry. 2011 Jun 20;17(26):7298-303. doi: 10.1002/chem.201100631. Epub 2011 May 12.

Abstract

The direct Pd-catalyzed oxidative coupling of two C-H-bonds within N-aryl-enamines 1 allows the efficient formation of differently substituted indoles 2. In this cross-dehydrogenative coupling, many different functional groups are tolerated and the starting material N-aryl-enamines 1 can be easily prepared in one step from commercially available anilines. In addition, the whole sequence can also be run in a one-pot fashion. Optimization data, mechanistic insight, substrate scope, and applications are reported in this full paper.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Aniline Compounds / chemistry*
  • Catalysis
  • Cyclization
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Palladium / chemistry*

Substances

  • Amines
  • Aniline Compounds
  • Indoles
  • Palladium