Visible-Light-Induced Selective Defluoroborylation of Polyfluoroarenes, gem-Difluoroalkenes, and Trifluoromethylalkenes

被引：0
|
作者：
Xu, Wengang [1 ,4 ]
Jiang, Heming [2 ]
Leng, Jing [1 ,3 ]
Ong, Han-Wee [1 ]
Wu, Jie [1 ,5 ]
机构：
[1] Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore,117543, Singapore
[2] Laboratory of Computational Chemistry & Drug Design, State Key Laboratory of Chemical Oncogenomics, Peking University, Shenzhen Graduate School, Shenzhen,518055, China
[3] State Key Laboratory of Silicate Materials for Architectures, Wuhan University of Technology, 122 Luoshi Road, Hubei, Wuhan,430070, China
[4] College of New Energy, Institute of New Energy, State Key Laboratory of Heavy Oil Processing, China University of Petroleum (East China), Qingdao,266580, China
[5] National University of Singapore (Suzhou) Research Institute, 377 Lin Quan Street, Suzhou Industrial Park, Jiangsu, Suzhou,215123, China
来源：
Advanced Materials | 2020年 / 59卷 / 10期
基金：
中国国家自然科学基金;
关键词：
Activation analysis - Atoms - Boron compounds - Catalysis - Organic compounds - Transition metals;
D O I：
10.1002/ANGE.201911819
中图分类号：
学科分类号：
摘要：
Fluorinated organoboranes serve as versatile synthetic precursors for the preparation of value-added fluorinated organic compounds. Recent progress has been mainly focused on the transition-metal catalyzed defluoroborylation. Herein, we report a photocatalytic defluoroborylation platform through direct B-H activation of N-heterocyclic carbene boranes, through the synergistic merger of a photoredox catalyst and a hydrogen atom transfer catalyst. This atomeconomic and operationally simple protocol has enabled defluoroborylation of an extremely broad scope of multifluorinated substrates including polyfluoroarenes, gem-difluoroalkenes, and trifluoromethylalkenes in a highly selective fashion. Intriguingly, the defluoroborylation protocol can be transition-metal free, and the regioselectivity obtained is complementary to the reported transition-metal-catalysis in many cases. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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收藏
页码：4038 / 4045
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