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Issue 26, 2012
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Copper-catalyzed oxidation of azolines to azoles

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Abstract

We report herein convenient, aerobic conditions for the oxidation of thiazolines to thiazoles and data regarding the oxidation mechanism. These reactions feature operationally simple and environmentally benign conditions and proceed in good yield to afford the corresponding azoles, thus enabling the inexpensive preparation of valuable molecular building blocks. Incorporation of a novel diimine-ligated copper catalyst, [(MesDABMe)CuII(OH2)3]2+ [OTf]2, provides increased reaction efficiency in many cases. In other cases copper-free conditions involving a stoichiometric quantity of base affords superior results.

Graphical abstract: Copper-catalyzed oxidation of azolines to azoles

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Publication details

The article was received on 05 Jan 2012, accepted on 28 Feb 2012 and first published on 29 Feb 2012


Article type: Paper
DOI: 10.1039/C2DT00025C
Dalton Trans., 2012,41, 7994-8002

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    Copper-catalyzed oxidation of azolines to azoles

    A. C. Dawsey, V. Li, K. C. Hamilton, J. Wang and T. J. Williams, Dalton Trans., 2012, 41, 7994
    DOI: 10.1039/C2DT00025C

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