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Synfacts 2014; 10(5): 0543
DOI: 10.1055/s-0033-1341136
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Click Reaction with Cu(II)-Triazine Dendrimer Immobilized on Nanosilica

Contributor(s):
Yasuhiro Uozumi
,
Hiroaki Tsuji
Nasr-Esfahani M, Mohammadpoor-Baltork I, * Khosropour AR, * Moghadam M, Mirkhani V, Tangestaninejad S, Rudbari HA. University of Isfahan, Iran
Copper Immobilized on Nanosilica Triazine Dendrimer (Cu(II)-TD@nSiO2)-Catalyzed Regioselective Synthesis of 1,4-Disubstituted 1,2,3-Triazoles and Bis- and Tris-Triazoles via a One-Pot Multicomponent Click Reaction.

J. Org. Chem. 2014;
79: 1437-1443
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Further Information

Publication History

Publication Date:
17 April 2014 (online)

 
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Key words

copper-triazine dendrimer - nanosilica - click reaction - alkynes - alkyl halides - sodium azide

Significance

A copper-triazine dendrimer immobilized on nanosilica [Cu(II)-TD@nSiO2] catalyzed the three-component reaction of terminal alkynes 1, alkyl halides 2, and sodium azide in the presence of sodium ascorbate to give the corresponding 1,4-disubstituted 1,2,3-triazoles 3 in up to 99% yield (23 examples).


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Comment

The authors previously reported the preparation of Cu(II)-TD@nSiO2 and its application to the dehydrogenative condensation of 1,2-phenylenediamine and 2-aminothiophenol with aromatic aldehydes (J. Mol. Catal. A: Chem. 2013, 379, 243). For the formation of 3a, the catalyst was recovered and reused seven times without significant loss of catalytic activity (7th reuse: 95% yield).


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