Iodide-Promoted Oxidative S-Arylation of Sulfenamides with Phenols for the Synthesis of Sulfilimines

Iodide-promoted oxidative S-arylation of sulfenamides with phenols is described for the synthesis of sulfilimines without the use of a transition-metal catalyst. Using TBAI and CHP, this iodide-promoted oxidative reaction affords aryl sulfilimines in variable yields. Control experiments are consistent with radical involvement and indicate that a free phenolic hydroxyl group is important for productive coupling under the standard conditions.