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Palladium catalyst immobilized on functionalized hyper–cross-linked polymers with 8-hydroxyquinoline as monomer for Suzuki–Miyaura coupling reactions

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Abstract

An efficient and stable palladium species catalyst immobilized on functionalized hyper–cross-linked polymers (HCPs-Pd) has been successfully developed and applied in the Suzuki–Miyaura coupling reaction of diverse types of aromatic halides with aryl boronic acid in this work. The results demonstrated that HCPs-Pd exhibited high catalytic activity, which benefited from the microporous structure of the catalyst guaranteed high dispersibility of active palladium, and high specific surface area, large pore volume, good chemical stability. Under optimal reaction conditions, 93.0% of biphenyl yield in the Suzuki–Miyaura reaction with bromobenzene (C6H5Br) and phenylboronic acid (C6H7BO2) as raw material was obtained. The good stability of the HCPs-II-Pd catalyst was verified by five cycles experiments. Perhaps this work provides new insights into the high-yield preparation of aromatic biphenyl compounds employing HCPs-Pd as an efficient and stable catalyst in the Suzuki–Miyaura reaction.

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Acknowledgements

The authors are grateful for the financial support of the Natural Science Foundation of Hunan Province (2021JJ30539, 2023JJ50450) and Innovative Training Project for College Students of China (S202310548066).

Funding

Funding was provided by Natural Science Foundation of Hunan Province (2021JJ30539, 2023JJ50450) and Innovative Training Project for College Students of China (S202310548066).

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Authors and Affiliations

  1. College of Chemistry and Materials, Huaihua University, Huaihua, 418000, People’s Republic of China

    Lu Feng, Sihang Lu, Haolei Zou, Gui Chen & Dexuan Xiang

  2. Hunan Engineering Laboratory for Preparation Technology of Polyvinyl Alcohol (PVA) Fiber Materia, Huaihua University, Huaihua, 418000, People’s Republic of China

    Dexuan Xiang

  3. Key Laboratory of Preparation and Application of Environmentally Friendly Functional Materials, Huaihua University, Huaihua, 418000, People’s Republic of China

    Gui Chen

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  1. Lu Feng
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  4. Gui Chen
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  5. Dexuan Xiang
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Contributions

LF contributed to conceptualization, investigation, data curation and writing—original draft. SL was involved in writing and editing and data curation. HZ contributed to conceptualization, investigation and data curation. GC was involved in conceptualization, methodology, formal analysis, investigation, writing—original draft, and writing—review and editing. DX contributed to conceptualization, supervision and project administration.

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Correspondence to Gui Chen or Dexuan Xiang.

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Feng, L., Lu, S., Zou, H. et al. Palladium catalyst immobilized on functionalized hyper–cross-linked polymers with 8-hydroxyquinoline as monomer for Suzuki–Miyaura coupling reactions. Res Chem Intermed 50, 2051–2066 (2024). https://doi.org/10.1007/s11164-024-05270-0

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