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


ABSTRACT: Regioselective amino-difluoromethylation of aromatic alkenes via C(sp3)-CF2H and C(sp3)-N bond formation with the C 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 1111111111111111111111111111111111 1111111111111111111111111111111111 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 1111111111111111111111111111111111 1111111111111111111111111111111111 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 C 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.

SUBMITTER: Noto N 

PROVIDER: S-EPMC5628600 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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

Noto Naoki N   Koike Takashi T   Akita Munetaka M  

Chemical science 20170710 9


Regioselective amino-difluoromethylation of aromatic alkenes <i>via</i> C(sp<sup>3</sup>)-CF<sub>2</sub>H and C(sp<sup>3</sup>)-N bond formation with the C[double bond, length as m-dash]C 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, <i>S</i>-difluoromethyl-<i>S</i>-di(<i>p</i>-xylyl)sulfonium tetrafluoroborate, and perylene catalysis is the key to the successful transformation. Furthermo  ...[more]

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