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Synfacts 2008(12): 1344-1344  
DOI: 10.1055/s-0028-1083559
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Huisgen 1,3-Dipolar Cycloaddition with an Ionic Polymer-Supported Copper(I) Catalyst

Contributor(s):Yasuhiro Uozumi, Yoshinori Hirai
U. Sirion, Y. J. Bae, B. S. Lee, D. Y. Chi*
Inha University, Inchon and FutureChem Co. Ltd., Seoul, Korea
Ionic Polymer Supported Copper(I): A Reusable Catalyst for Huisgen’s 1,3-Dipolar Cycloaddition
Synlett  2008,  2326-2330  
Thieme Connect
Further Information

Publication History

Publication Date:
20 November 2008 (online)

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Key words

Huisgen 1,3-di-polar cycloaddition - CuI-immobilized ionic polymers - click chemistry

Significance

The ionic polymer-supported copper(I) (1) catalyzed the Huisgen 1,3-cycloaddition reaction of azides and terminal alkynes in t-BuOH-H2O to give the corresponding 1,4-disubstituted 1,2,3-triazoles in 36-99% yield (12 examples). In the reaction of 4-methoxybenzylazide and phenyl­acetylene, catalyst 1 was recovered by filtration and reused ten times without significant loss of catalytic activity (1st-10th runs: 100% conversions).

Comment

The ionic polymer-supported copper(I) with BF4- or MsO- as a counter anion exhibited higher catalytic activity in the Huisgen cycloaddition, whereas significant leaching of CuI was observed during the reaction. Leaching of CuI also occurred when the reaction was carried out in DMF-H2O, MeCN-H2O or DMSO-H2O.

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