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Synlett 2008(15): 2326-2330  
DOI: 10.1055/s-2008-1078245
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Ionic Polymer Supported Copper(I): A Reusable Catalyst for Huisgen’s 1,3-Dipolar Cycloaddition

Uthaiwan Siriona, Yu Jin Baea, Byoung Se Leea,b, Dae Yoon Chi*a,b
a Department of Chemistry, Inha University, 253 Yonghyundong Namgu, Inchon 402-751, Korea
Fax: +82(32)8675604; e-Mail: dychi@inha.ac.kr;
b Research Institute of Labeling, FutureChem Co. Ltd., 388-1 Pungnap-2-dong, Songpagu, Seoul 138-736, Korea
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Publication History

Received 1 April 2008
Publication Date:
31 July 2008 (online)

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Abstract

A series of CuI-immobilized polymeric supports having quaternary ammonium salts were prepared as recyclable heterogeneous catalysts with evaluation of their ability in Cu(I)-catalyzed Huisgen’s 1,3-dipolar cycloaddition of azides and terminal alkynes, a ‘click reaction’. An ionic polymer possessing an acetate anion was suitable as the solid support for immobilization of CuI and CuI-immobilized compound showed negligible leaching levels of CuI, providing 1,4-disubstituted 1,2,3-triazoles in good yields, regio-selectively. The CuI-immobilized compound was also reused not only up to ten times without any loss of yield or catalytic activity, but also for twelve different click reactions.

Key words

Huisgen 1,3-dipolar cycloaddition - click reaction - CuI-immobilized ionic polymer - recyclable solid catalyst

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