Abstract:

Compounds containing sulfinamide and sulfinamidine (i.e. sulfinamid(in)e) motifs are burgeoning within drug discovery due to their unique biological properties. These motifs are also useful synthons toward accessing valuable sulfur(VI) derivatives such as sulfonamides, sulfonimidamides, and sulfondiimidamides. The most practiced routes to sulfinamid(in)es engage sulfinylamine and sulfurdiimide reagents with prefunctionalized starting materials such as organometallic reagents, boroxines, and carboxylic acids. However, the most idyllic route to install sulfinamid(in)e functionality would be to directly couple C–H bonds with sulfinylamine and sulfurdiimide reagents. To this end, I propose a research program centered around leveraging a transition metal catalyzed C–H insertion approach to allow for direct access to sulfinamid(in)e functionality. This protocol would provide the first direct approach to sulfinamide(in)es and, owing to synthetic versatility of these motifs, provide access to important sulfur(VI) derivatives.