Deprotonative C–H Silylation of Functionalized Arenes and Heteroarenes Using Trifluoromethyltrialkylsilane with Fluoride

A highly selective C-H silylation reaction of functionalized arenes and heteroarenes was developed using Ruppert-Prakash reagent (TMSCF3) activated by alkali metal fluoride. TMSCF3 is considered to play dual roles as a precursor of a mild base and also as a silicon electrophile. The silylation is compatible with sensitive functional groups such as halogen and nitro groups.