Herein we report the first synthesis of borylfuroxans via the reaction of sulfonylfuroxans with Lewis base-ligated boranes under radical conditions. As a synthetic application, the transformation of borylfuroxans to a range of 1,2-dioximes and their derivatives is demonstrated.
Photocatalytic C–F Bond Borylation of Polyfluoroarenes with NHC-boranes
作者:Peng-Ju Xia、Zhi-Peng Ye、Yuan-Zhuo Hu、Jun-An Xiao、Kai Chen、Hao-Yue Xiang、Xiao-Qing Chen、Hua Yang
DOI:10.1021/acs.orglett.0c00020
日期:2020.3.6
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.