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Visible‐Light‐Induced Selective Defluoroborylation of Polyfluoroarenes, gem ‐Difluoroalkenes, and Trifluoromethylalkenes
Author(s) -
Xu Wengang,
Jiang Heming,
Leng Jing,
Ong HanWee,
Wu Jie
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201911819
Subject(s) - catalysis , regioselectivity , chemistry , combinatorial chemistry , boranes , transition metal , carbene , photoredox catalysis , photochemistry , nanotechnology , photocatalysis , organic chemistry , materials science , boron
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.