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Generation of the SCF 3 Radical by Photoredox Catalysis: Intra‐ and Intermolecular Carbotrifluoromethylthiolation of Alkenes
Author(s) -
Dagousset Guillaume,
Simon Cédric,
Anselmi Elsa,
Tuccio Béatrice,
Billard Thierry,
Magnier Emmanuel
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700734
Subject(s) - intermolecular force , electron paramagnetic resonance , photochemistry , chemistry , photoredox catalysis , catalysis , yield (engineering) , spin trapping , photocatalysis , radical , aryl , quantum yield , radical ion , organic chemistry , materials science , fluorescence , molecule , nuclear magnetic resonance , physics , alkyl , quantum mechanics , metallurgy , ion
We report the first use of N ‐trifluoromethylthiosaccharin as the source of SCF 3 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 SCF 3 ‐containing products in good to excellent yield. Importantly, the formation of this SCF 3 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.