3 years ago

Lewis Acid Promoted Single C–F Bond Activation of the CF3 Group: SN1′-Type 3,3-Difluoroallylation of Arenes with 2-Trifluoromethyl-1-alkenes

Lewis Acid Promoted Single C–F Bond Activation of the CF3 Group: SN1′-Type 3,3-Difluoroallylation of Arenes with 2-Trifluoromethyl-1-alkenes
Hibiki Hatta, Kohei Fuchibe, Rie Oki, Junji Ichikawa, Ken Oh
Activation of the sp3 C−F bond in 2-trifluoromethyl-1-alkenes was accomplished through treatment with a Lewis acid. In the presence of an equimolar amount of EtAlCl2, the (trifluoromethyl)alkenes readily underwent an SN1′-type reaction with arenes through a Friedel–Crafts-type mechanism via elimination of a fluoride ion to afford 3,3-difluoroallylated arenes in good yields. This selective activation of one C−F bond of the CF3 group provides a synthetic method for accessing biologically and synthetically important 1,1-difluoro-1-alkenes. A clean break: C−F bond activation in 2-trifluoromethyl-1-alkenes was accomplished through treatment with a Lewis acid. In the presence of EtAlCl2, the (trifluoromethyl)alkenes readily undergo elimination of a F− ion and SN1′-type reaction with arenes through a Friedel–Crafts-type mechanism to give 3,3-difluoroallylated arenes in good yields. This selective activation of just one sp3 C−F bond of the CF3 group provides facile access to 1,1-difluoro-1-alkenes.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201701985

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