Regioselective Formation of 2,5-Disubstituted Oxazoles Via Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes

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2011

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Ingeniería Química, Química Física y Ciencias de los Materiales

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CIQSO

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http://hdl.handle.net/10272/11553

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10.1021/ja109732s

Abstract

The reaction of 1-alkynes with acylazides 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 CuAAC type, that constitutes a significant variation of the commonly observed [3+2] cycloaddition reaction to yield 1,2,3-triazoles

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Cano. I.. Álvarez, E., Nicasio Jaramillo, M.C., Pérez Romero, P.J.: "Regioselective Formation of 2,5-Disubstituted Oxazoles Via Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes". Journal of the American Chemical Society. Vol 133, págs. 191-193, (2011). DOI: 10.1021/ja109732s

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