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

An operationally simple transition-metal-free protocol for the arylation of α-(trifluoromethyl)­styrene derivatives with silicon-protected functionalized aryl pronucleophiles is disclosed. Catalytic amounts of an anionic Lewis base such as fluoride trigger the release of the aryl nucleophile from N-aryl-N′-silyldiazenes by desilylation along with denitrogenation. The thus-generated carbon nucleophiles engage in an allylic displacement with α-(trifluoromethyl)­styrene electrophiles to afford the corresponding geminal difluoroalkenes.