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Synthesis 2008(3): 363-368  
DOI: 10.1055/s-2008-1032037
PAPER
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of 1,2,3-Triazoles by Use of a Silica-Supported Copper(I) Catalyst

Tao Miaoa, Lei Wang*a,b
a Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, P. R. of China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(561)3090518; e-Mail: leiwang@hbcnc.edu.cn;
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Publication History

Received 12 September 2007
Publication Date:
10 January 2008 (online)

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Abstract

A 1,3-dipolar cycloaddition reaction catalyzed by copper(I) immobilized on organic-inorganic hybrid materials was developed. Terminal alkynes reacted with benzyl- or alkyl halides and sodium azide in the presence of a copper(I) catalyst immobilized on 3-aminopropyl- or 3-[(2-aminoethyl)amino]propyl-functionalized silica gel in ethanol. The reactions exclusively generated the corresponding regiospecific 1,4-disubstituted 1,2,3-triazoles in good to excellent yields. The azide intermediates do not need to be isolated during this procedure, and this should prove to be useful especially when unstable low-molecular-weight and polyvalent azides are used. Furthermore, the silica-supported copper could be recovered and recycled by simple filtration of the reaction solution and reused for ten consecutive trials without decrease in activity.

Key words

1,2,3-triazoles - supported catalysis - organic-inorganic hybrid material - copper(I) catalyst - 1,3-dipolar cycloaddition