Primary Sulfonamide Synthesis Using the Sulfinylamine Reagent <i>N</i>-Sulfinyl-<i>O</i>-(<i>tert</i>-butyl)hydroxylamine, <i>t</i>-BuONSO.

Davies TQ, Tilby MJ, Skolc D, Hall A, Willis MC

Sulfonamides have played a defining role in the history of drug development and continue to be prevalent today. In particular, primary sulfonamides are common in marketed drugs. Here we describe the direct synthesis of these valuable compounds from organometallic reagents and a novel sulfinylamine reagent, <i>t</i>-BuONSO. A variety of (hetero)aryl and alkyl Grignard and organolithium reagents perform well in the reaction, providing primary sulfonamides in good to excellent yields in a convenient one-step process.