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Electrochemically driven regioselective C−H phosphorylation of group 8 metallocenes

Author

Listed:
  • Hao Zheng

    (Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Chang-Hui Liu

    (Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Shi-Yu Guo

    (Dalian Institute of Chemical Physics, Chinese Academy of Sciences)

  • Gu-Cheng He

    (Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Xiang-Ting Min

    (Dalian Institute of Chemical Physics, Chinese Academy of Sciences)

  • Bo-Chao Zhou

    (Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Ding-Wei Ji

    (Dalian Institute of Chemical Physics, Chinese Academy of Sciences)

  • Yan-Cheng Hu

    (Dalian Institute of Chemical Physics, Chinese Academy of Sciences)

  • Qing-An Chen

    (Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

Abstract

Metallocenes are privileged backbones for synthesis and catalysis. However, the direct dehydrogenative C−H functionalization of unsymmetric metallocenes suffers from reactivity and selectivity issues. Herein, we report an electrochemically driven regioselective C−H phosphorylation of group 8 metallocenes. Mechanistic investigations indicate this dehydrogenative cross coupling occurs through an electrophilic radical substitution of the metallocene with a phosphoryl radical, facilitated by the metallocene itself. This work not only offers an efficient and divergent synthesis of phosphorylated metallocenes, but also provides a guide to interpret the reactivity and regioselectivity for the C−H functionalization of unsymmetric metallocenes.

Suggested Citation

  • Hao Zheng & Chang-Hui Liu & Shi-Yu Guo & Gu-Cheng He & Xiang-Ting Min & Bo-Chao Zhou & Ding-Wei Ji & Yan-Cheng Hu & Qing-An Chen, 2022. "Electrochemically driven regioselective C−H phosphorylation of group 8 metallocenes," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31178-7
    DOI: 10.1038/s41467-022-31178-7
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    References listed on IDEAS

    as
    1. Hao Long & Chong Huang & Yun-Tao Zheng & Zhao-Yu Li & Liang-Hua Jie & Jinshuai Song & Shaobin Zhu & Hai-Chao Xu, 2021. "Electrochemical C–H phosphorylation of arenes in continuous flow suitable for late-stage functionalization," Nature Communications, Nature, vol. 12(1), pages 1-7, December.
    2. Peng Xiong & Huai-Bo Zhao & Xue-Ting Fan & Liang-Hua Jie & Hao Long & Pin Xu & Zhan-Jiang Liu & Zheng-Jian Wu & Jun Cheng & Hai-Chao Xu, 2020. "Site-selective electrooxidation of methylarenes to aromatic acetals," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
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