title: Visible Light-Induced Photoredox Construction of Trifluoromethylated Quaternary Carbon Centers from Trifluoromethylated Tertiary Bromides.
abstract: A mild, operationally simple, visible light-induced photoredox method for constructing novel trifluoromethylated quaternary carbon centers from trifluoromethylated tertiary bromides has been developed. Using this method, a wide range of alkenes were successfully bifunctionalized to γ-butyrolactams. As for electron-rich alkenes, reactions catalyzed by Ir(dF(CF3)ppy)2(dtbbpy)(PF6) were kinetic processes with high yields and short times. For styrenes, reactions catalyzed by Ir(ppy)2(dtbbpy)(PF6) were thermodynamic processes with moderate yields and prolonged reaction times. For aliphatic alkenes, the reactions were neither thermodynamic nor kinetic and fac-Ir(ppy)3 was used as catalyst. Thus, reactions were not as efficient as electron-rich alkenes. The atom-transfer radical addition reactions of trifluoromethylated tertiary bromides with alkynes were also achieved. The configuration of products we separated was E type only. Some of the products exhibited bactericidal activity.
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai, 200032, P. R. of China.
authors.forename: Feng
authors.initials: F
authors.lastname: Huan
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai, 200032, P. R. of China.
authors.forename: Qing-Yun
authors.initials: QY
authors.lastname: Chen
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai, 200032, P. R. of China.
authors.forename: Yong
authors.initials: Y
authors.lastname: Guo
mesh_terms: D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D055668:Photochemical Processes
chemical_list: D001965:Bromides; D006845:Hydrocarbons, Fluorinated