SN2′ Defluorinative Allylation of Trifluoromethylalkenes with Allylsilanes

Abstract

An SN2’ defluorinative allylation of trifluoromethylalkenes with readily available allylsilanes to access homoallyl gem-difluoroalkenes was reported. The reaction is triggered by catalytic amount of TBAF with the extruded fluoride in reaction serving as the sustainable activator for organosilanes. The high efficiency, good functional group tolerance, and mild reaction conditions enable the potential utility of this method in synthetic chemistry.

Fluoride-Catalyzed Arylation of α-(Trifluoromethyl)styrene Derivatives with Silicon-Masked, Functionalized Aryl Pronucleophiles

“…α-(Trifluoromethyl)­styrene derivatives are common substrates for C–F bond activation in organic chemistry . Numerous transition-metal-catalyzed as well as metal-free protocols for the synthesis of 1,1-difluoroalkenes starting from α-(trifluoromethyl)­styrenes through (formal) S N 2′ mechanisms were reported involving various types of nucleophiles. − Although alkylation and allylation of α-(trifluoromethyl)­styrene derivatives were extensively studied, arylation strategies have been less investigated so far. Only a few transition-metal-free arylation procedures were described using organometallic compounds under relatively harsh conditions and, hence, are quite limited in terms of substrate scope and functional-group tolerance.…”