In situ prepared CuI nanoparticles on modified poly(styrene-co-maleic anhydride): an efficient and recyclable catalyst for the azide–alkyne click reaction in water

Abstract

A facile, high-yielding and straightforward methodology for the copper-catalyzed synthesis of 1,4-disubstituted 1,2,3-triazoles in water, using in situ prepared copper nanoparticles (NPs) on modified poly(styrene-co-maleic anhydride) [SMA] catalyst, is reported. The polymer support was easily prepared from the reaction of SMA with 4-aminopyridine and subsequently underwent reaction with CuI NPs. The catalyst was applied for the preparation of triazoles under air, followed by chromatographic separation of the products. The polymer-supported catalyst not only showed high catalytic activity but also showed high 1,4-regioselectivity for the [3 + 2] Huisgen cycloaddition in water as solvent. The products were obtained in good to excellent yields in all cases. The catalyst can be used without pre-activation and reloaded for at least five runs without significant decrease in its activity. The catalyst was characterized by SEM, energy dispersive spectroscopy analysis of X-rays, and inductively coupled plasma.

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Acknowledgments

M. M. H is thankful to Iran National Science Foundation for partial financial assistance.

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Correspondence to Majid M. Heravi.

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Hashemi, E., Beheshtiha, Y.S., Ahmadi, S. et al. In situ prepared CuI nanoparticles on modified poly(styrene-co-maleic anhydride): an efficient and recyclable catalyst for the azide–alkyne click reaction in water. Transition Met Chem 39, 593–601 (2014). https://doi.org/10.1007/s11243-014-9838-5

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Keywords

  • Triazole
  • Inductively Couple Plasma
  • Alkyl Halide
  • Cycloaddition Reaction
  • Phenylacetylene