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Triazole-Functionalized Silica Supported Palladium(II) Complex: A Novel and Highly Active Heterogeneous Nano-catalyst for C–C Coupling Reactions in Aqueous Media

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Abstract

Two novel triazole-modified silica supports A and B were successfully prepared via “click” reaction of azide-functionalized SiO2 with propargyl alcohol (A) and propargyl amine (B), in which the click-triazole as an important functional entity, in addition to a molecular linker, provides capabilities of metal coordination as an excellent chelator. Treatment of the resulting click-supports with Pd(OAc)2 afforded the click-catalysts A and B, which were well characterized and evaluated in Suzuki–Miyaura coupling in terms of activity and recyclability in H2O/EtOH solvent. The catalyst A showed more reasonable results and so, was applied as a highly efficient and recyclable catalyst in the coupling reactions of various aryl halides with phenylboronic acid under phosphine-free and low Pd loading conditions.

Graphical Abstract

Two novel nano pd-catalysts were successfully prepared by immobilization of Pd(OAc)2 onto the silica supports containing the nitrogen-rich triazole chelators and were investigated in Suzuki–Miyaura coupling in aqueous solvent.

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Acknowledgements

We gratefully acknowledge the funding support received for this project from the Isfahan University of Technology (IUT), IR of Iran, and Isfahan Science and Technology Town (ISTT), IR of Iran. Further financial support from the Center of Excellence in Sensor and Green Chemistry Research (IUT) is gratefully acknowledged.

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Authors and Affiliations

  1. Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, 84156, Isfahan, Islamic Republic of Iran

    Abdol Reza Hajipour & Fatemeh Mohammadsaleh

  2. Department of Pharmacology, Medical School, University of Wisconsin, 1300 University Avenue, Madison, WI, 53706-1532, USA

    Abdol Reza Hajipour

Authors
  1. Abdol Reza Hajipour
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  2. Fatemeh Mohammadsaleh
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Correspondence to Abdol Reza Hajipour.

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Hajipour, A.R., Mohammadsaleh, F. Triazole-Functionalized Silica Supported Palladium(II) Complex: A Novel and Highly Active Heterogeneous Nano-catalyst for C–C Coupling Reactions in Aqueous Media. Catal Lett 148, 1035–1046 (2018). https://doi.org/10.1007/s10562-018-2316-5

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  • DOI: https://doi.org/10.1007/s10562-018-2316-5

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