One-Pot Synthesis of N-Iodo Sulfoximines from Sulfides

J Org Chem. 2021 Apr 16;86(8):5991-6000. doi: 10.1021/acs.joc.1c00292. Epub 2021 Mar 25.

Abstract

This is the first report on the synthesis and characterization of N-iodo sulfoximines. The synthesis was designed as a room temperature one-pot cascade reaction from readily available sulfides as starting compounds, converted into sulfoximines by reaction with ammonium carbonate and (diacetoxyiodo)benzene, followed by iodination with N-iodosuccinimide or iodine in situ, in up to 90% isolated yields, also at a multigram scale. Iodination of aryls with N-iodo sulfoximines, oxidation, and conversion to N-SCF3 congeners have been demonstrated.