Visible‐Light‐Induced Selective Defluoroborylation of Polyfluoroarenes, gem‐Difluoroalkenes, and Trifluoromethylalkenes. Issue 10 (23rd January 2020)

• Record Type: Journal Article
• Authors: Xu, Wengang; Jiang, Heming; Leng, Jing; Ong, Han‐Wee; Wu, Jie
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 10(2020)
• Page Start: 4009
• Page End: 4016
• Publication Date: 2020-01-23
• Subjects: boryl radical -- defluoroborylation -- hydrogen atom transfer -- photocatalysis -- polyfluoroarene; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201911819
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : A practical and selective defluoroborylation of polyfluoroarenes, gem ‐difluoroalkenes, and trifluoromethylalkenes was developed through photoredox and hydrogen atom transfer induced B−H activation to synthesize fluorinated organoboranes as the building blocks for value‐added organofluorine compounds.