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Electrophotocatalytic Undirected C-H Trifluoromethylations of (Het)Arenes.

ABSTRACT: Electrophotochemistry has enabled arene C-H trifluoromethylation with the Langlois reagent CF3 SO2 Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant-free approach for the generation of the CF3 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.

SUBMITTER: Qiu Y

PROVIDER: S-EPMC7155051 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Electrophotocatalytic Undirected C-H Trifluoromethylations of (Het)Arenes.

Qiu Youai Y Scheremetjew Alexej A Finger Lars H LH Ackermann Lutz L

Chemistry (Weinheim an der Bergstrasse, Germany) 20200219 15

Electrophotochemistry has enabled arene C-H trifluoromethylation with the Langlois reagent CF3 SO2 Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant-free approach for the generation of the CF3 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 o ...[more]

PMID: 31875327

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