Sulfonimidamidation Reagent for Three-Component Reaction

(Triphenylmethyl)thionyl imide (TrNSO) is a useful reagent for one-pot synthesis of sulfonimideamides. TrNSO is added with Grignard reagents and then treated with tert-butyl hypochlorite to generate a sulfonimidoyl chloride 2. Subsequent addition of the amine with methanesulfonic acid provided the corresponding sulfonimide amide in good yield. This reaction is applicable to various aromatic and alkyl Grignard reagents, as well as primary and secondary amines. Furthermore, 3 which can be obtained from 3,4-dimethoxybenzylamine can be easily deprotected by ammonium cerium(IV) nitrate (CAN) to afford the free sulfonimide amide. TrNSO is anticipated to be used in the synthesis of sulfonimideamides relevant to sulfonamides in drug discovery.