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Electrochemical C−C bond cleavage of cyclopropanes towards the synthesis of 1,3-difunctionalized molecules

Author

Listed:
  • Pan Peng

    (Wuhan University)

  • Xingxiu Yan

    (Wuhan University)

  • Ke Zhang

    (Wuhan University)

  • Zhao Liu

    (Wuhan University)

  • Li Zeng

    (Wuhan University)

  • Yixuan Chen

    (Wuhan University)

  • Heng Zhang

    (Wuhan University)

  • Aiwen Lei

    (Wuhan University
    King Abdulaziz University)

Abstract

Electrochemistry has a lot of inherent advantages in organic synthesis and many redox reactions have been achieved under electrochemical condition. However, the electrochemical C−C bond cleavage and functionalization reactions are less studied. Here we develop electrochemical C−C bond cleavage and 1,3-difuntionalization of arylcyclopropanes under catalyst-free and external-oxidant-free conditions. 1,3-difluorination, 1,3-oxyfluorination and 1,3-dioxygenation of arylcyclopropanes are achieved with a high chemo- and regioselectivity by the strategic choice of nucleophiles. This protocol has good functional groups tolerance and can be scaled up. Mechanistic studies demonstrate that arylcyclopropane radical cation obtained from the anode oxidation and the subsequently generated benzyl carbonium are the key intermediates in this transformation. This development provides a scenario for constructing 1,3-difunctionalized molecules.

Suggested Citation

  • Pan Peng & Xingxiu Yan & Ke Zhang & Zhao Liu & Li Zeng & Yixuan Chen & Heng Zhang & Aiwen Lei, 2021. "Electrochemical C−C bond cleavage of cyclopropanes towards the synthesis of 1,3-difunctionalized molecules," Nature Communications, Nature, vol. 12(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-23401-8
    DOI: 10.1038/s41467-021-23401-8
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