title: Efficient Cu-catalyzed atom transfer radical addition reactions of fluoroalkylsulfonyl chlorides with electron-deficient alkenes induced by visible light.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Florida, PO Box 117200, Gainesville, Florida, 32611-7200 (USA).
authors.forename: Xiao-Jun
authors.initials: XJ
authors.lastname: Tang
authors.forename: William R
authors.initials: WR
authors.lastname: Dolbier
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004583:Electrons; D005609:Free Radicals / Q000737:chemistry; D008027:Light; D013441:Sulfinic Acids / Q000737:chemistry*
chemical_list: D000475:Alkenes; D005609:Free Radicals; D013441:Sulfinic Acids; C044255:sulfonyl chloride; D003300:Copper
keywords: atom transfer radical addition reactions; copper; fluorine; photoredox catalysis; radicals