Visible Light-Induced 1,2-Diphenyldisulfane-Mediated Defluoroborylation of Polyfluoroarenes

作者：Qiao‐Jing Pan, Yuqi Miao, Hou‐Ji Cao, Zhenxing Liu, Xuenian Chen · 发表于：The Journal of Organic Chemistry · 年份：2024 · DOI：10.1021/acs.joc.4c00286 · 被引用次数：7 · 研究领域：Fluorine in Organic Chemistry、Radical Photochemical Reactions、Sulfur-Based Synthesis Techniques

A green and practical protocol of defluoroborylation of polyfluoroarenes with stable and readily accessible NHC-borane was developed, using 1,2-diphenyldisulfane as a hydrogen atom transfer (HAT) and single electron transfer (SET) reagent precursor under visible-light irradiation, leading to the concise formation of value-added fluorinated organoboron scaffolds. Mechanism studies revealed the method underwent a boryl radical addition reaction with polyfluoroarene, followed by successive single electron transfer pathways and defluorination of the C-F bond to offer the targeted product. This unprecedented platform relies on 1,2-diphenyldisulfane and base without using expensive photocatalysts, highlighting the methodology has promising application value to prepare borylated polyfluoroarene compounds.