Activation of the sp 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 , the (trifluoromethyl)alkenes readily underwent an S 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 group provides a synthetic method for accessing biologically and synthetically important 1,1-difluoro-1-alkenes.
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 Facile Synthesis of 1,1-Difluoroallenes from Commercially Available 1,1,1-Trifluoro-2-iodoethane. -The lithiation of 1,1,1-trifluoro-2-iodoethane (I) followed by reaction with aldehydes (II) or ketone (VI) and subsequent acetylation of resulting alcohols give rise to corresponding iodoallylic acetates (IV) and (VIII), which are readily converted into desired 1,1-difluoroallenes (V) and (IX), resp., on treatment with zinc in DMF. -(OH, K.; FUCHIBE, K.; ICHIKAWA*, J.; Synthesis 2011, 6, 881-886, http://dx.
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