Palladium-Catalyzed Sulfinamidation of Aryl Chlorides.

The transition-metal-catalyzed addition of aryl halides to N-sulfinylamines is a valuable method for the synthesis of aza-sulfur functional groups. However, to date, the substrate scope has been limited to aryl iodides and bromides. Here, we report the Pd-catalyzed sulfinamidation of aryl chlorides using sulfinylamine reagent TIPS-NSO, which exploits the lower cost, greater commercial availability, and broader structural diversity of aryl chloride substrates. The reaction tolerates a broad range of (hetero)aryl chloride substrates, including pharmaceutically relevant examples. The Pd loading can be reduced to 2.5 mol %, and the reactions can be conducted on a gram scale.