A Rapid, Mild and Direct Route to Sulfonimidoyl Fluoride from Sulfenamide

We develop a rapid and mild protocol to access sulfonimidoyl fluoride-[S(VI)] from sulfenamide-[S(II)] directly. The transformation occurs via the reaction of sulfenamide with NCS (<i>N</i>-chlorosuccinimide), water, and TBAF in acetonitrile. Water and TBAF act as the source for S═O bond formation and fluoride, respectively. The reaction takes a very short time (within 5 min). The drug molecules, such as Carbamazepine and Levetiracetam attached sulfonimidoyl fluorides are also achieved following this protocol. Furthermore, sulfonimidoyl fluoride is transformed into sulfonimidamide in the presence of AlCl₃. To the best of our knowledge, it is the first report detailing the synthesis of sulfonimidoyl fluoride-[S(VI)] directly from S(II)-sulfenamide.