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Visible-Light-Induced Selective Defluoroborylation of Polyfluoroarenes, gem-Difluoroalkenes, and Trifluoromethylalkenes.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2019-12-18 , DOI: 10.1002/anie.201911819
Wengang Xu 1, 2 , Heming Jiang 3 , Jing Leng 1, 4 , Han-Wee Ong 1 , Jie Wu 1, 5
Affiliation  

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.

中文翻译:

可见光诱导的多氟芳烃,宝石-二氟烯烃和三氟甲基烯烃的选择性脱氟硼化。

氟化有机硼烷可作为通用的合成前体,用于制备增值的氟化有机化合物。最近的进展主要集中在过渡金属催化的脱氟硼化作用上。在本文中,我们报告了通过光氧化还原催化剂和氢原子转移催化剂的协同合并,通过直接BH活化N-杂环卡宾硼烷的光催化脱氟硼化平台。这种原子经济且操作简单的方案能够以高度选择性的方式对包括聚氟芳烃,宝石-二氟烯烃和三氟甲基烯烃在内的多种氟化底物进行极为广泛的脱氟硼化。有趣的是,脱氟硼化协议可以不含过渡金属,
更新日期:2020-01-23
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