title: Visible-Light-Promoted Trifluoromethylthiolation of Styrenes by Dual Photoredox/Halide Catalysis.
abstract: Herein, we report a new visible-light-promoted strategy to access radical trifluoromethylthiolation reactions by combining halide and photoredox catalysis. This approach allows for the synthesis of vinyl-SCF3 compounds of relevance in pharmaceutical chemistry directly from alkenes under mild conditions with irradiation from household light sources. Furthermore, alkyl-SCF3-containing cyclic ketone and oxindole derivatives can be accessed by radical-polar crossover semi-pinacol and cyclization processes. Inexpensive halide salts play a crucial role in activating the trifluoromethylthiolating reagent towards photoredox catalysis and aid the formation of the SCF3 radical.
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
authors.forename: Roman
authors.initials: R
authors.lastname: Honeker
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
authors.forename: R Aleyda
authors.initials: RA
authors.lastname: Garza-Sanchez
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany. glorius@uni-muenster.de.
authors.forename: Matthew N
authors.initials: MN
authors.lastname: Hopkinson
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany. matthew.hopkinson@uni-muenster.de.
authors.forename: Frank
authors.identifier: http://orcid.org/0000-0002-0648-956X
authors.initials: F
authors.lastname: Glorius
mesh_terms: D002384:Catalysis; D003500:Cyclization; D006219:Halogens / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008027:Light; D015394:Molecular Structure; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D013343:Styrenes / Q000737:chemistry*
chemical_list: D006219:Halogens; D006845:Hydrocarbons, Fluorinated; D013343:Styrenes
keywords: halides; photocatalysis; synthetic methods; trifluoromethylthiolation; visible light