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

Pan Peng, Xingxiu Yan, Ke Zhang, Zhao Liu, Li Zeng, Yixuan Chen, Heng Zhang () and Aiwen Lei ()
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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

Nature Communications, 2021, vol. 12, issue 1, 1-7

Abstract: 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.

Date: 2021
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DOI: 10.1038/s41467-021-23401-8

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