title: Generation of the SCF3Radical by Photoredox Catalysis: Intra- and Intermolecular Carbotrifluoromethylthiolation of Alkenes.
abstract: We report the first use of N-trifluoromethylthiosaccharin as the source of SCF3radical under photoredox catalysis. This allowed an efficient and general visible-light-mediated carbotrifluoromethylthiolation of alkenes. Under the optimized conditions using fac-[Ir(ppy)3] as the photocatalyst, various N-aryl acrylamides as well as a wide range of substituted styrenes can readily be difunctionalized in an intra- or intermolecular fashion, affording the corresponding SCF3-containing products in good to excellent yield. Importantly, the formation of this SCF3radical along with other key radical intermediates was unambiguously demonstrated thanks to spin trapping/electron paramagnetic resonance (ST/EPR) experiments, which enabled a clear understanding of the reaction mechanism.
authors.affiliation: Institut Lavoisier de Versailles, UMR 8180, Université de Versailles-Saint-Quentin, 78035, Versailles Cedex, France.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Dagousset
authors.affiliation: Institut Lavoisier de Versailles, UMR 8180, Université de Versailles-Saint-Quentin, 78035, Versailles Cedex, France.
authors.forename: Cédric
authors.initials: C
authors.lastname: Simon
authors.affiliation: Institut Lavoisier de Versailles, UMR 8180, Université de Versailles-Saint-Quentin, 78035, Versailles Cedex, France.|Infectiologie et Santé Publique (ISP), UMR INRA 1282, Université de Tours, Parc de Grandmont, 37200, Tours, France.
authors.forename: Elsa
authors.initials: E
authors.lastname: Anselmi
authors.affiliation: Aix-Marseille Université-CNRS, Institut de Chimie Radicalaire (UMR 7273), 13397, Marseille Cedex 20, France.
authors.forename: Béatrice
authors.initials: B
authors.lastname: Tuccio
authors.affiliation: Institute of Chemistry and Biochemistry (ICBMS-UMR 5246), Université Lyon 1, CNRS, 69622, Villeurbanne, France.
authors.forename: Thierry
authors.initials: T
authors.lastname: Billard
authors.affiliation: Institut Lavoisier de Versailles, UMR 8180, Université de Versailles-Saint-Quentin, 78035, Versailles Cedex, France.
authors.forename: Emmanuel
authors.identifier: http://orcid.org/0000-0003-3392-3971
authors.initials: E
authors.lastname: Magnier
keywords: EPR spectroscopy; carbotrifluoromethylthiolation; photoredox catalysis; radicals; trifluoromethylthiosaccharin