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.
The selectivea ctivation of one CÀFb ond (single activation) of the CF 3 group on cyclopropanes was achieved for the first time. When (trifluoromethyl)cyclopropanes were treated with arenes,a llylsilanes, silyl enol ethers,o rh ydrosilanesi nt he presence of Me 2 AlCl, fluoride elimination andt he subsequent ring openingp roceeded to afford 4,4-difluorohomoallylated products.I nt he absence of external nucleophiles,a na lkyl group of AlR 3 was effectively introduced to provide the corresponding 1,1-difluoroalkenes.
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.
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