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Lewis Acid Promoted Single C–F Bond Activation of the CF 3 Group: S N 1′‐Type 3,3‐Difluoroallylation of Arenes with 2‐Trifluoromethyl‐1‐alkenes
Author(s) -
Fuchibe Kohei,
Hatta Hibiki,
Oh Ken,
Oki Rie,
Ichikawa Junji
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201701985
Subject(s) - chemistry , trifluoromethyl , lewis acids and bases , group (periodic table) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , alkyl
Activation of the sp 3 C−F bond in 2‐trifluoromethyl‐1‐alkenes was accomplished through treatment with a Lewis acid. In the presence of an equimolar amount of EtAlCl 2 , the (trifluoromethyl)alkenes readily underwent an S N 1′‐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 CF 3 group provides a synthetic method for accessing biologically and synthetically important 1,1‐difluoro‐1‐alkenes.