Iron-Catalyzed Amination of Sulfides and Sulfoxides with Azides in Photochemical Continuous Flow Synthesis

A photochemical (UVA) continuous flow process for the amination of thioethers and sulfoxides was performed with trichloroethoxysulfonyl azide in the presence of catalytic iron(III) acetylacetonate. Aromatic and aliphatic sulfilimines and sulfoximines were produced in high yields and short reaction times. The reaction with chiral sulfoxides was stereospecific, producing enantioenriched sulfoximines in excellent yields.