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Effective Suzuki coupling reaction enabled by palladium–polycarbene catalyst derived from porous polyimidazolium

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Abstract

N-heterocyclic-carbene based polymers with abundant active sites and excellent stability are fascinating and highly desired while remain rare for the lack of easy synthetic protocols. In this article, an unprecedented strategy that employed a porous polyimidazolium (IPF-CSU-4) as the support for Pd(II) coordination was proposed to develop efficient heterogeneous catalyst. IPF-CSU-4 was constructed via a one-step quaternization chemistry between 2,4,6-tris(1-imidazolyl)-1,3,5-triazine and 1,4-bis(chloromethyl)benzene. The in-situ complexation of palladium (Pd) with carbene ligand of the polyimidazolium readily afforded a Pd-loaded porous polymeric network (Pd-PPc-4) with high stability. Pd-PPc-4 showed favorable accessibility to seven aryl halides substrates in Suzuki coupling reactions, with a catalytic yield up to 99% under mild conditions (3 h, 60 °C) and no obvious loss of activity even after five catalytic cycles. This provides new pathways for developing highly-efficient and stable catalysts through porous organic polymers for typical organic transformations.

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Acknowledgements

We acknowledge the financial support from the National Science Foundation of China (Nos. 21674129, 51873232 and 21636010).

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  1. College of Chemistry and Chemical Engineering, Central South University, Changsha, 410083, People’s Republic of China

    Xiaofeng Li, Xiaoyun Yu, Weijie Zhang, Chunyue Pan, Juntao Tang & Guipeng Yu

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Appendix: Supplementary data

Appendix: Supplementary data

Synthetic route of 2,4,6-tris(1-imidazolyl)-1,3,5-triazine (Fig. S1), (a) 1H NMR spectrum; (b) 13C NMR spectrum; and (c) FT-IR spectrum of triimidazolyl triazine (Fig. S2), FT-IR spectra of IPF-CSU-4 obtained at 70°C, 120°C, 150°C, and 180°C (Fig. S3), SEM spectroscopy of (a) IPF-CSU-4 and (b) Pd-PPc-4 (Fig. S4), TEM spectroscopy of Pd-PPc-4 (Fig. S5), (a) CH4 and (b) CO2 adsorption/desorption isotherms of IPF-CSU-4 and Pd-PPc-4 (Fig. S6), Mass spectrum of IPF-CSU-4 (Fig. S7), Proposed mechanism of Suzuki reaction catalyzed by Pd-PPc-4 (Fig. S8), Pore parameters of the polymers IPF-CSU-4 and Pd-PPc-4 (Table S1), Catalytic condition optimization of Suzuki coupling reaction (Table S2), 1H NMR spectrum of catalytic products (Figs. S9–11).

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Li, X., Yu, X., Zhang, W. et al. Effective Suzuki coupling reaction enabled by palladium–polycarbene catalyst derived from porous polyimidazolium. J Porous Mater 29, 601–608 (2022). https://doi.org/10.1007/s10934-021-01193-y

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