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Heterogeneous Copper-Free Sonogashira Cross-Coupling Reactions Catalyzed by a Recyclable Orthopalladated Azo-Complex

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Abstract

In this work, the preparation of titania-supported Pd catalyst deriving from pincer-type orthopalladated azo-complex is presented. The new highly dispersed Pd catalyst was prepared through a pH-controlled adsorption method and fully characterized by FT-IR, XRD, TGA, FE-SEM, TEM and N2 adsorption/desorption techniques. The Pd/TiO2 nano-catalyst was then applied as an efficient heterogeneous catalyst for copper-free Sonogashira cross-coupling reactions of a representative range of aryl iodides, bromides, and chlorides with phenylacetylene with the very low catalyst Pd-loading. The coupling products were obtained in high yields in environmentally friendly reaction media. The catalyst was successfully recycled over six runs, with no significant loss of catalytic activity.

Graphical Abstract

A titania-supported heterogeneous Pd catalyst derived from pincer-type orthopalladated complex is prepared and used as a reusable efficient catalyst in the Sonogashira cross-coupling reactions in green media.

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Acknowledgements

We gratefully acknowledge the Department of Chemistry, Isfahan University of Technology (IUT).

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Authors and Affiliations

  1. Department of Chemistry, Isfahan University of Technology, Isfahan, 84156/83111, Iran

    Kazem Karami, Mahdieh Afroomand & Parvaneh Bayat

  2. Faculty of Chemistry, Kharazmi University, Tehran, 15719-14911, Iran

    Sedigheh Abedanzadeh

  3. Department of Chemistry, University of Vigo, 36310, Vigo, Spain

    Pablo Hervés

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  1. Kazem Karami
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  2. Sedigheh Abedanzadeh
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  3. Mahdieh Afroomand
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  4. Pablo Hervés
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  5. Parvaneh Bayat
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Correspondence to Kazem Karami.

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Karami, K., Abedanzadeh, S., Afroomand, M. et al. Heterogeneous Copper-Free Sonogashira Cross-Coupling Reactions Catalyzed by a Recyclable Orthopalladated Azo-Complex. Catal Lett 153, 1438–1449 (2023). https://doi.org/10.1007/s10562-022-04059-3

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  • DOI: https://doi.org/10.1007/s10562-022-04059-3

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