Synlett 2013; 24(7): 843-846
DOI: 10.1055/s-0032-1318488
letter
© Georg Thieme Verlag Stuttgart · New York

2-Ethynylpyridine-Promoted Rapid Copper(I) Chloride Catalyzed Azide–Alkyne Cycloaddition Reaction in Water

Hidekatsu Hiroki
Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga Bunkyo-ku, Tokyo 112-8551, Japan   Fax: +81(3)38171895   Email: orgsynth@kc.chuo-u.ac.jp
,
Kenichi Ogata
Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga Bunkyo-ku, Tokyo 112-8551, Japan   Fax: +81(3)38171895   Email: orgsynth@kc.chuo-u.ac.jp
,
Shin-ichi Fukuzawa*
Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga Bunkyo-ku, Tokyo 112-8551, Japan   Fax: +81(3)38171895   Email: orgsynth@kc.chuo-u.ac.jp
› Author Affiliations
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Publication History

Received: 28 January 2013

Accepted after revision: 28 February 2013

Publication Date:
18 March 2013 (online)


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Abstract

The copper(I) chloride catalyzed reaction of azides with alkynes in water at room temperature was promoted by the addition of a catalytic amount of 2-ethynylpyridine, affording the corresponding 1,4-disubstituted 1,2,3-triazoles in good yields after a specific reaction time. The catalytic system could be successfully applied to electron-rich, electron-poor, and sterically crowded substrates. A study of the additive effect of pyridine derivatives revealed that alkynyl and 2-pyridyl groups were essential for activating the copper catalyst.

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