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Electrophotocatalytic Undirected C−H Trifluoromethylations of (Het)Arenes
Author(s) -
Qiu Youai,
Scheremetjew Alexej,
Finger Lars H.,
Ackermann Lutz
Publication year - 2020
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.201905774
Subject(s) - trifluoromethylation , reagent , chemistry , catalysis , electrosynthesis , combinatorial chemistry , electron transfer , flow chemistry , photoredox catalysis , photochemistry , organic chemistry , computational chemistry , trifluoromethyl , photocatalysis , alkyl , electrode , electrochemistry
Electrophotochemistry has enabled arene C−H trifluoromethylation with the Langlois reagent CF 3 SO 2 Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant‐free approach for the generation of the CF 3 radical. The electrophotochemistry was carried out in an operationally simple manner, setting the stage for challenging C−H trifluoromethylations of unactivated arenes and heteroarenes. The robust nature of the electrophotochemical manifold was reflected by a wide scope, including electron‐rich and electron‐deficient benzenes, as well as naturally occurring heteroarenes. Electrophotochemical C−H trifluoromethylation was further achieved in flow with a modular electro‐flow‐cell equipped with an in‐operando monitoring unit for on‐line flow‐NMR spectroscopy, providing support for the single electron transfer processes.