Electroreductive deuteroarylation of alkenes enabled by an organo-mediator
Xinling Li, Jianfeng Zhou, Weijie Deng, Ziliang Wang, Yating Wen, Zhenjie Li, Youai Qiu, Yubing Huang
Abstract
O as the deuterium source. The key to the protocol lies in the employment of a catalytic amount of 2,2'-bipyiridine as an efficient organo-mediator, which facilitates the generation of aryl radicals by assisting in the cleavage of the C-X (X = I or Br) bonds in aryl halides. Because its reduction potential matches that of aryl iodides, the organo-mediator can control the chemoselectivity of the reaction and avoid the side reactions of competitive substrate deuteration. These phenomena are theoretically supported by CV experiments and DFT calculations. Our protocol provides a series of mono-deuterated alkylarenes with excellent deuterium incorporation through two single-electron reductions (SER), without requiring metal catalysts, external reductants, and sacrificial anodes.