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Synthesis of Pd/conjugated microporous polymer heterogeneous catalysts via imine groups and high catalytic efficiency on Suzuki–Miyaura coupling reaction

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Abstract

Four kinds of conjugated microporous polymers (CMPs) with imine structures were synthesized by a Sonogashira coupling reaction followed by a postreaction between aldehydes and amines. Palladium nanoparticles (Pd NPs) were successfully supported on the CMPs to prepare Pd/CMP heterogeneous catalysts and were used to catalyze the Suzuki–Miyaura coupling reaction. The number of aromatic nuclei and nitrogen atoms in the CMPs highly affects Pd loading. In the Suzuki–Miyaura coupling reaction, the Pd/CMP with good Pd NPs dispersibility and appropriate Pd content (Pd/CMP-NA) exhibited the highest catalytic efficiency with 100% conversion and 95.4% yield which can be used for many substrates. The Pd/CMP-NA heterogeneous catalyst was easy to recover and still exhibited good catalytic efficiency after 5 cycles. To further understand the catalytic mechanism of Pd/CMP-NA on the Suzuki–Miyaura coupling reaction, we proposed a rational catalytic cycle. This paper provides an idea for the structural design of CMPs used for Suzuki–Miyaura catalytic reaction.

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Acknowledgements

This research was funded by the National Natural Science Foundation of China, grant number 52173202; the Heilongjiang Science Foundation Project, grants number YQ2022116;the Fundamental Research Funds in Heilongjiang Provincial universities (135309348).

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Authors and Affiliations

  1. College of Materials Science and Engineering, Qiqihar University, Wenhua Street 42, Qiqihar, 161006, Heilongjiang, China

    Yu Zang, Shan Gao, Boyu Jing, Hong Sun, Jianjun Wang & Jiao Liu

  2. Jiangsu Engineering Laboratory of Novel Functional Polymeric Materials, Soochow University, Suzhou, 215123, China

    Yu Zang

  3. College of Communications and Electronics Engineering, Qiqihar University, Wenhua Street 42, Qiqihar, 161006, Heilongjiang, China

    Fengjuan Miao

  4. Analysis and Testing Center, Qiqihar University, Wenhua Street 42, Qiqihar, 161006, Heilongjiang, China

    Liang Xu

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  1. Yu Zang
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Contributions

Y.Z. performed writing—review and editing. S.G. performed writing—original draft. B.J., H.S., J.W., J.L., and F.M. performed data curation. L.X. contributed to methodology and data curation.

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Correspondence to Yu Zang or Liang Xu.

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Zang, Y., Gao, S., Jing, B. et al. Synthesis of Pd/conjugated microporous polymer heterogeneous catalysts via imine groups and high catalytic efficiency on Suzuki–Miyaura coupling reaction. J Mater Sci 58, 170–185 (2023). https://doi.org/10.1007/s10853-022-08032-8

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