Friedel-Crafts alkylation of pentafluorobenzene

Substitution Effect on the Cylization/Fluorination Reaction ofN-Dienes in Superacid

“…This original dehydrofluorination/fluorination process seems to come from the intramolecular Friedel−Crafts reaction, followed by dehydrofluorination (rearomatization)/fluorination. As Friedel Crafts alkylation of polyfluorobenzenes requires relatively harsh conditions, to support our hypothesis, the reactivity of substrate 3h′ was tested. In similar conditions, the fluorinated isoquinoline 4h′′ was formed in 41% yield (entry 9).…”

Polyhalomethanes Combined with Lewis Acids in Alkane Chemistry

“…Thus far, the alkylation of aromatics even with traditional alkylating agents has mainly been limited to weakly passivated arenes, such as monohalobenzenes and polyfluoroarenes, which are slightly deactivated toward electrophiles. The alkylation of deactivated arenes with alkanes and cycloalkanes has been carried out for the first time. , For instance, propane alkylates pentafluorobenzene in the presence of CBr 4 • n AlBr 3 ( n = 1 or 2) at 0 °C for 1.5 h to give pentafluoroisopropylbenzene in almost quantitative yield 164 (Scheme ).…”

“…Pentafluorobenzene was reported to react in the presence of AlCl 3 at 150 °C with CH 2 Cl 2 to give (C 6 F 5 ) 2 CH 2 in 77% yield after 4.5 h and with CHCl 3 to give (C 6 F 5 ) 3 CH in 92% yield after 8 h …”

Friedel−Crafts Alkylation of Polychlorobenzenes with (1,2-Dichloroethyl)trichlorosilane

“…Although the alkylation of polyhalogenated benzenes such as trichlorobenzene and polyfluorinated benzenes with polychlorinated methanes has been reported to give alkylation products, the yields were low due to the deactivation effects of the electron- withdrawing halogen substituents. To the best of our knowledge, the analogous alkylations of polychlorinated benzenes with organosilanes have never been reported.…”