Efficient Cu‐catalyzed Atom Transfer Radical Addition Reactions of Fluoroalkylsulfonyl Chlorides with Electron‐deficient Alkenes Induced by Visible Light

作者：Xiaojun Tang, William R. Dolbier · 发表于：Angewandte Chemie International Edition · 年份：2015 · DOI：10.1002/anie.201412199 · 被引用次数：426 · 研究领域：Fluorine in Organic Chemistry、Radical Photochemical Reactions、Sulfur-Based Synthesis Techniques

Fluoroalkylsulfonyl chlorides, R(f)SO2Cl, in which R(f)=CF3, C4F9, CF2H, CH2F, and CH2CF3, are used as a source of fluorinated radicals to add fluoroalkyl groups to electron-deficient, unsaturated carbonyl compounds. Photochemical conditions, using Cu mediation, are used to produce the respective α-chloro-β-fluoroalkylcarbonyl products in excellent yields through an atom transfer radical addition (ATRA) process. Facile nucleophilic replacement of the α-chloro substituent is shown to lead to further diverse functionalization of the products.