Structure–Reactivity Relationship of Trifluoromethanesulfenates: Discovery of an Electrophilic Trifluoromethylthiolating Reagent

A family of electrophilic trifluoromethanesulfenates
was prepared.
Structure–reactivity relationship studies showed that the substituted
groups on the aryl ring of the trifluoromethylthiolating reagent did
not have an obvious influence on their reactivities. A simplified
electrophilic trifluoromethylthiolating reagent 1c was
then identified that can react with a wide range of nucleophiles such
as Grignard reagents, arylboronic acids, alkynes, indoles, β-ketoesters,
oxindoles, and sodium sulfinates under mild reaction conditions. A
variety of functional groups were tolerated under these conditions.