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Photocatalytic Trifluoromethylthiolation of Aromatic Alkenes Associated with Hydroxylation and Alkoxylation
Author(s) -
Li Yanjie,
Koike Takashi,
Akita Munetaka
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600562
Subject(s) - chemistry , reagent , vicinal , photocatalysis , regioselectivity , hydroxylation , photoredox catalysis , redox , electrophile , pyrrolidine , electrophilic aromatic substitution , alkoxy group , photochemistry , catalysis , organic chemistry , combinatorial chemistry , alkyl , enzyme
A photoredox‐catalyzed trifluoromethylthiolation process of aromatic alkenes has been developed. A strongly reducing photocatalyst, fac ‐[Ir(4‐MeO‐ppy) 3 ] (4‐MeO‐ppy=2‐pyridyl‐5‐methoxyphenyl), and an electrophilic trifluoromethylthiolating reagent, 1‐(trifluoromethylthio)pyrrolidine‐2,5‐dione ( 1 a ), play key roles in the efficient generation of a trifluoromethansulfenyl radical ( . SCF 3 ). The well‐designed photoredox system induces a single‐step, regioselective installation of a CF 3 S and a hydroxy or an alkoxy group onto vicinal carbon atoms through redox‐neutral processes. The present oxytrifluoromethylthiolation features mild reaction conditions without extra additives for the activation of the CF 3 S reagent, making the present protocol applicable to a wide variety of functionalized aromatic alkenes.