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Efficient Cu‐catalyzed Atom Transfer Radical Addition Reactions of Fluoroalkylsulfonyl Chlorides with Electron‐deficient Alkenes Induced by Visible Light
Author(s) -
Tang XiaoJun,
Dolbier William R.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201412199
Subject(s) - chemistry , substituent , radical , catalysis , electron transfer , photochemistry , nucleophile , surface modification , medicinal chemistry , atom (system on chip) , nucleophilic addition , organic chemistry , computer science , embedded system
Fluoroalkylsulfonyl chlorides, R f SO 2 Cl, in which R f =CF 3 , C 4 F 9 , CF 2 H, CH 2 F, and CH 2 CF 3 , 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.