SO2F2-Mediated N-Alkylation of Imino-Thiazolidinones

Abstract

The N-alkylation of ambident and weakly nucleophilic imino-thiazolidinones has been developed via substitution with alkyl fluorosulfonates. These reactive electrophiles are obtained through the transformation of nontoxic, economic, and commercially available alcohol derivatives on exposure to SO₂F₂ gas. The use of electron-withdrawing groups and DMAc as solvent affords a (Z)- and N-endocyclic selectivity for the easy introduction of a variety of alkyl and polyfluoroalkyl chains.