N-Iodosuccinimide-Mediated Synthesis of Benzo-Fused Bisimidazoles Enabled by a One-Pot Tandem Reaction of Fluorinated Propargyl Amidines

A N-iodosuccinimide (NIS)-mediated divergent and efficient tandem reaction between fluorinated propargyl amidines and aromatic o-diamines without any metal catalyst and additive under mild reaction conditions was developed for the synthesis of benzo-fused bisimidazoles in moderate to excellent yields. Preliminary mechanistic studies suggested that this reaction proceeded by an intermediate of secondary amine derived from 5-iodomethyl imidazole, and NIS played another role of oxidation reagent to promote the formation of a benzimidazole motif.