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Synthesis of 5-substituted 1H-tetrazoles from aryl halides using nanopolymer-anchored palladium(II) complex as a new heterogeneous and reusable catalyst

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Abstract

This paper reports on the preparation and use of chloromethylated polystyrene-anchored palladium(II) complex, [Ps-ttet-Pd(II)], as a separable nanocatalyst for the synthesis of 5-substituted 1H-tetrazoles by treating aryl halides with K4[Fe(CN)6] as non-toxic cyanide source, to generate in situ the corresponding aryl nitriles which then react through [2 + 3] cycloaddition with sodium azide. High yields of the products, simple methodology, easy work-up procedure, high catalytic activity, and superior cycling stability of the catalyst are the main advantages of this protocol. The structure of the catalyst was characterized using the powder XRD, SEM, TG-DTA, EDS, AAS, and FT-IR spectroscopy techniques.

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Acknowledgments

We gratefully acknowledge the Iranian Nano Council and Universities of Mazandaran and Qom for the support of this work.

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Authors and Affiliations

  1. Faculty of Chemistry, University of Mazandaran, Babolsar, Iran

    Mahmood Tajbakhsh, Heshmatollah Alinezhad & Taghi A. Kamali

  2. Department of Chemistry, Faculty of Science, University of Qom, P. O. Box 37185-359, Qom, Iran

    Mahmoud Nasrollahzadeh

  3. Center of Environmental Researches, University of Qom, Qom, Iran

    Mahmoud Nasrollahzadeh

Authors
  1. Mahmood Tajbakhsh
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  2. Heshmatollah Alinezhad
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  3. Mahmoud Nasrollahzadeh
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  4. Taghi A. Kamali
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Corresponding author

Correspondence to Mahmoud Nasrollahzadeh.

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Tajbakhsh, M., Alinezhad, H., Nasrollahzadeh, M. et al. Synthesis of 5-substituted 1H-tetrazoles from aryl halides using nanopolymer-anchored palladium(II) complex as a new heterogeneous and reusable catalyst. Monatsh Chem 147, 2135–2142 (2016). https://doi.org/10.1007/s00706-016-1732-8

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  • DOI: https://doi.org/10.1007/s00706-016-1732-8

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