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A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes

Authors

  • Vsevolod V. Rostovtsev Dr.,

    1. Department of Chemistry and the Skaggs Institute for Chemical Biology The Scripps Research Institute, BCC-315 10550 N. Torrey Pines Rd., La Jolla, CA 92037 (USA) Fax: (+1) 858-784-7562
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  • Luke G. Green Dr.,

    1. Department of Chemistry and the Skaggs Institute for Chemical Biology The Scripps Research Institute, BCC-315 10550 N. Torrey Pines Rd., La Jolla, CA 92037 (USA) Fax: (+1) 858-784-7562
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  • Valery V. Fokin Prof.,

    1. Department of Chemistry and the Skaggs Institute for Chemical Biology The Scripps Research Institute, BCC-315 10550 N. Torrey Pines Rd., La Jolla, CA 92037 (USA) Fax: (+1) 858-784-7562
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  • K. Barry Sharpless Prof.

    1. Department of Chemistry and the Skaggs Institute for Chemical Biology The Scripps Research Institute, BCC-315 10550 N. Torrey Pines Rd., La Jolla, CA 92037 (USA) Fax: (+1) 858-784-7562
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  • We thank the National Institute of General Medical Sciences, the National Institutes of Health (GM 28384), the National Science Foundation (CHE-9985553), and the W. M. Keck Foundation for financial support. We also thank Dr. F. Himo, Prof. L. Noodleman, Prof. Flavio Grynszpan, and Prof. M. G. Finn for helpful discussions.

Abstract

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By simply stirring in water, organic azides and terminal alkynes are readily and cleanly converted into 1,4-disubstituted 1,2,3-triazoles through a highly efficient and regioselective copper(I)-catalyzed process (see scheme for an example).

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