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-(Methyld3) arylsulfonothioates represent a kind of powerful deuterated methylthiolating reagent and allow modular trideuteromethylthiolation with a variety of nucleophiles or electrophiles including diazonium salts, beta-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.

Automated summary

A family of electrophilic deuterated methylthiolating reagents has been developed, which can be synthesized from inexpensive d4-MeOH in a few steps with high yields. These reagents serve as powerful tools for deuterated methylthiolation reactions with various nucleophiles or electrophiles under mild conditions. The structure-reactivity research conducted in this study opens up a new avenue for the development of deuterated methylthiolating reagents and efficient methodologies for trideuteromethylthiolation.