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

Peng-Ju XiaZhi-Peng YeYuan-Zhuo HuJun-An XiaoKai ChenHao-Yue XiangXiao-Qing ChenJun-An Xiao
Published in: Organic letters (2020)
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.
Keyphrases
  • electron transfer
  • room temperature
  • visible light
  • ionic liquid
  • randomized controlled trial
  • high resolution
  • high throughput
  • mass spectrometry
  • highly efficient