Copper-catalysed intramolecular O-arylation: a simple and efficient method for benzoxazole synthesis

Org Biomol Chem. 2014 Dec 21;12(47):9696-701. doi: 10.1039/c4ob02068e. Epub 2014 Oct 28.

Abstract

A wide range of 2-substituted benzoxazoles can be efficiently synthesized from N-(2-iodo-/bromo-phenyl)benzamides, and even the less reactive N-(2-chlorophenyl)benzamides, via Cu-catalysed intramolecular coupling cyclization reactions using methyl 2-methoxybenzoate as the ligand under mild reaction conditions. In addition, the benzoxazoles can be easily prepared from the primary amides coupling with o-dihalobenzenes in a single step.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Benzamides / chemistry*
  • Benzoxazoles / chemical synthesis*
  • Benzoxazoles / chemistry
  • Catalysis
  • Copper / chemistry*
  • Cyclization
  • Halogenation
  • Hydroxybenzoate Ethers / chemistry
  • Ligands
  • Salicylates / chemistry

Substances

  • Amides
  • Benzamides
  • Benzoxazoles
  • Hydroxybenzoate Ethers
  • Ligands
  • Salicylates
  • 2-methoxybenzoic acid
  • benzamide
  • Copper