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多氟芳烃与N-杂环卡宾硼烷的光催化C-F键硼化反应

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

作者信息

Xia Peng-Ju, Ye Zhi-Peng, Hu Yuan-Zhuo, Xiao Jun-An, Chen Kai, Xiang Hao-Yue, Chen Xiao-Qing, Yang Hua

机构信息

College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.

Key Laboratory of Hunan Province for Water Environment and Agriculture Product Safety, Central South University, Changsha 410083, P. R. China.

出版信息

Org Lett. 2020 Mar 6;22(5):1742-1747. doi: 10.1021/acs.orglett.0c00020. Epub 2020 Feb 13.

Abstract

The first photoredox-catalyzed defluoroborylation of polyfluoroarenes with NHC-BH 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.

摘要

首例多氟芳烃与NHC-BH的光氧化还原催化脱氟硼化反应已在室温下通过单电子转移(SET)/自由基加成途径轻松实现。这种新策略充分利用了光氧化还原催化的优势,通过直接活化B-H键生成关键的硼自由基。良好的官能团耐受性和高区域选择性为该方法在制备各种有价值的多氟芳基硼化合物方面提供了无与伦比的优势。此外,还进行了计算和实验研究以阐明反应机理。

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