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Fluorinated Sulfilimino Iminiums: Efficient and Versatile Sources of Perfluoroalkyl Radicals under Photoredox Catalysis
Author(s) -
Daniel Marion,
Dagousset Guillaume,
Diter Patrick,
Klein PierreAndré,
Tuccio Béatrice,
Goncalves AnneMarie,
Masson Géraldine,
Magnier Emmanuel
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201700290
Subject(s) - photoredox catalysis , radical , chemistry , photochemistry , cationic polymerization , reagent , photocatalysis , spin trapping , electron paramagnetic resonance , catalysis , sulfoxide , organic chemistry , physics , nuclear magnetic resonance
Reported herein is the use of S‐perfluoroalkyl sulfilimino iminiums as a new source of R F radicals under visible‐light photoredox catalysis (R F =CF 3 , C 4 F 9 , CF 2 Br, CFCl 2 ). These shelf‐stable perfluoroalkyl reagents, readily prepared on gram scale from the corresponding sulfoxide using a one‐pot procedure, allow the efficient photoredox‐induced oxyperfluoroalkylation of various alkenes using fac‐Ir(ppy) 3 as the photocatalyst. Importantly, spin‐trapping/electron paramagnetic resonance experiments were carried out to characterize all the radical intermediates involved in this radical/cationic process.