TBAF-assisted copper-catalyzed N-arylation and benzylation of benzazoles with aryl and benzyl halides under the ligand/base/ solvent-free conditions

J Org Chem. 2009 Aug 7;74(15):5675-8. doi: 10.1021/jo900752z.

Abstract

TBAF-assisted N-arylation and benzylation of benzazoles such as 1H-benzimidazole, 1H-indole, and 1H-benzotriazole with aryl and benzyl halides have been demonstrated under the ligand/base/solvent-free conditions. In the presence of CuBr2 and TBAF (n-Bu4NF), the azoles underwent N-arylation and benzylation with aryl and benzyl halides smoothly in moderate to good yields. It is noteworthy that the reaction is conducted under the ligand/base/solvent-free conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzimidazoles / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Hydrocarbons, Halogenated / chemistry*
  • Indoles / chemistry*
  • Molecular Structure
  • Quaternary Ammonium Compounds / chemistry*
  • Stereoisomerism
  • Triazoles / chemistry*

Substances

  • Benzimidazoles
  • Hydrocarbons, Halogenated
  • Indoles
  • Quaternary Ammonium Compounds
  • Triazoles
  • Copper
  • benzotriazole
  • tetrabutylammonium
  • benzimidazole