期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 10, 页码 4009-4016出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201911819
关键词
boryl radical; defluoroborylation; hydrogen atom transfer; photocatalysis; polyfluoroarene
资金
- Ministry of Education (MOE) of Singapore [MOE2017-T2-2-081]
- GSK-EDB [R-143-000-687-592]
- NUS (Suzhou) Research Institute
- National Natural Science Foundation of China [21702142, 21871205]
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 atom-economic 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.
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