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Silver and Copper-Supramolecular Coordination Polymers Inspired Alkyne–Azide Click Reactions

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Abstract

Two 3D-supramolecular coordination polymers (SCP); {[SnMe3(bpe)] [Ag(CN)2].2H2O}, 1, (bpe) = 1,2-bis(4-pyridyl)ethane and {[CuI(CN)(phen)2][CuII(CN)2(phen)]·5H2O}, 2, (phen) = phenanthroline, have been synthesized and characterized by physicochemical and spectroscopic methods. The SCP 1 and 2 exhibit good catalytic activity for the formation of substituted triazoles (1-benzyl- 4-bromomethyl triazole and 1-benzyl-4-phenyl triazole) in 98–100% yield. Of the factors investigated, the ratio of reactants and the amount of catalyst had the largest impact on yield. The use of the SCP 2 reduced by sodium ascorbate gave generally higher yields than a direct source of Cu owing to the high degree of efficiency. The general utility of the catalyst 1 and 2 indicated the formation of 1,4-substituted 1,2,3-triazoles in very good yield at shorter time in direct comparison to reactions performed in the presence of catalysts Cu(OAc)2 and AgNO3. In this case, the SCP 1 and 2-catalyzed alkyne–azide cyclo-addition provide 1,4-disubstituted 1,2,3-triazoles with such efficiency and scope that the transformation has been described as “click” chemistry.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Tanta, Tanta, 31527, Egypt

    Safaa Eldin H. Etaiw, Ibrahim A. Salem & Alaa Tawfik

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  1. Safaa Eldin H. Etaiw
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  2. Ibrahim A. Salem
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  3. Alaa Tawfik
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Correspondence to Safaa Eldin H. Etaiw.

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Etaiw, S.E.H., Salem, I.A. & Tawfik, A. Silver and Copper-Supramolecular Coordination Polymers Inspired Alkyne–Azide Click Reactions. J Inorg Organomet Polym 27, 215–224 (2017). https://doi.org/10.1007/s10904-016-0465-9

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