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

• Record Type: Journal Article
• Authors: Xu, Wengang; Jiang, Heming; Leng, Jing; Ong, Han‐Wee; Wu, Jie
• Is Part Of: Angewandte Chemie. Volume 132:Number 10(2020)
• Page Start: 4038
• Page End: 4045
• Publication Date: 2020-01-23
• Subjects: Borylradikale -- Defluorborylierung -- Wasserstoffatomtransfer -- Photokatalyse -- Polyfluorarene; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201911819
• Languages: English
• ISSNs: 0044-8249

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 : Die selektive Defluorborylierung von Polyfluorarenen, gem ‐Difluoralkenen und Trifluormethylalkenen gelingt durch Photoredox‐ und Wasserstoffatomtransfer‐induzierte B‐H‐Aktivierung. Die Reaktionen liefern fluorierte Organoborane als Bausteine für höherwertige Organofluorverbindungen.