Copper oxidation reaction

September 21, 2014 – 07:00 am

Highly Regioselective Synthesis of NO2-Substituted 1,2,3-Triazoles

School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China

Org. Lett., 2015, 17 (5), pp 1118–1121

DOI: 10.1021/ol503687w

Abstract

A new copper-catalyzed [3 + 2] cycloaddition/oxidation reaction of nitro-olefins with organic azides has been developed to afford 1, 4(-NO2), 5-trisubstituted 1, 2, 3-triazoles. This reaction sequence has a broad substrate scope and affords NO2-substituted 1, 2, 3-triazoles with high regioselectivities and in good to excellent yields. The involved oxidative process overcomes the elimination of HNO2 for general cycloaddition of nitro-olefins with organic azides, which shows a high atom economy and potential applications.

General experimental procedure, characterization data of the compounds, and CIF data for 3b and 3p. This material is available free of charge via the Internet at .

Source: pubs.acs.org

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