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1. Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis

Author

Naoki Noto, Munetaka Akita, and Takashi Koike

Subjects
Tetrafluoroborate, 010405 organic chemistry, Trifluoromethylation, Sulfonium, Photoredox catalysis, Regioselectivity, General Chemistry, 010402 general chemistry, Photochemistry, 01 natural sciences, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, chemistry, Moiety, Perylene
Abstract

Regioselective amino-difluoromethylation of aromatic alkenes via C(sp3)–CF2H and C(sp3)–N bond formation with the CC moiety has been achieved in a single operation by visible-light photoredox catalysis. The combination of a shelf-stable and easy-to-handle sulfonium salt, S-difluoromethyl-S-di(p-xylyl)sulfonium tetrafluoroborate, and perylene catalysis is the key to the successful transformation. Furthermore, this noble metal-free protocol allows for the photocatalytic trifluoromethylation of alkenes.

Published
2017

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