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

Organic & Biomolecular Chemistry Pub Date: 2014-10-20 DOI: 10.1039/C4OB02068E

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.

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