Fluoride-Catalyzed Arylation of α-(Trifluoromethyl)styrene Derivatives with Silicon-Masked, Functionalized Aryl Pronucleophiles
Aliyaah J. M. Rahman, Y. XU, Martin Oestreich
Abstract
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.
Topics & Concepts
ChemistryNucleophileTrifluoromethylArylGeminalElectrophileAllylic rearrangementCatalysisFluorideStyreneOrganic chemistryLewis acids and basesCombinatorial chemistryAlkylInorganic chemistryCopolymerPolymerFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsCyclopropane Reaction Mechanisms