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- Title
Generation of the SCF<sub>3</sub> Radical by Photoredox Catalysis: Intra- and Intermolecular Carbotrifluoromethylthiolation of Alkenes.
- Authors
Dagousset, Guillaume; Simon, Cédric; Anselmi, Elsa; Tuccio, Béatrice; Billard, Thierry; Magnier, Emmanuel
- Abstract
We report the first use of N-trifluoromethylthiosaccharin as the source of SCF3 radical 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 SCF3 radical 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.
- Subjects
CHEMICAL radical synthesis; ALKENE derivatives; STYRENE; PHOTOCATALYSTS; ELECTRON paramagnetic resonance; REACTION mechanisms (Chemistry)
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 18, p4282
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201700734