Photocatalytic C-F Bond Borylation of Polyfluoroarenes with NHC-boranes.

Peng-Ju Xia,Zhi‐Peng Ye,Yuan‐Zhuo Hu,Jun‐An Xiao,Kai Chen,H. Xiang,Xiaoqing Chen,Hua Yang

Published 2020 in Organic Letters

ABSTRACT

The first photoredox-catalyzed defluoroborylation of polyfluoroarenes with NHC-BH3 has been facilely achieved at room temperature via a single-electron-transfer (SET)/radical addition pathway. This new strategy makes full use of the advantage of photoredox catalysis to generate the key boryl radical via direct activation of a B-H bond. Good functional group tolerance and high regioselectivity offer this protocol incomparable advantages in preparing a wide array of valuable polyfluoroarylboron compounds. Moreover, both computational and experimental studies were performed to illustrate the reaction mechanism.

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