Regioselective formation of 2,5-disubstituted oxazoles via copper(I)-catalyzed cycloaddition of acyl azides and 1-alkynes

Description

The reaction of 1-alkynes with acyl azides in the presence of [Tpm *,BrCu(NCMe)]BF4 [Tpm*,Br = tris(3,5-dimethyl-4-bromopyrazolyl)methane] as the catalyst provides 2,5-oxazoles in moderate to high yields. This is a novel transformation of the CuAAC type that constitutes a significant variation of the commonly observed [3 + 2] cycloaddition reaction to yield 1,2,3-triazoles.

Abstract

Ministerio de Educación y Cultura CTQ2008-00042/BQU, CSD2006-003

Abstract

Junta de Andalucía P07-FQM-02745

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