S-(Methyl-d3) Arylsulfonothioates: A Family of Robust, Shelf-Stable, and Easily Scalable Reagents for Direct Trideuteromethylthiolation

A family of electrophilic deuterated methylthiolating reagents, S-(methyl-d3) arylsulfonothioates, was developed in two or three steps from cheap d4-MeOH in high yields. S-(Methyl-d3) arylsulfonothioates represent a kind of powerful deuterated methylthiolating reagent and allow modular trideuteromethylthiolation with a variety of nucleophiles or electrophiles including aryl(hetero) iodides, boronic acids esters, terminal alkynes, diazonium salts, β-ketoester, and oxindole under mild reaction conditions. A structure–reactivity research (SAR) study was conducted and provided a new avenue for the development of deuterated methylthiolating reagents and efficient methodology for trideuteromethylthiolation.