Fe(III)-Catalyzed N-Amidomethylation of Secondary and Primary Anilines with TosMIC

Abstract

A Fe­(III)-catalyzed N-amidomethylation of secondary and primary anilines with p-toluenesulfonylmethyl isocyanide (TosMIC) in water is described. TosMIC plays dual roles as the source of methylene as well as an amidating reagent to form α-amino amides in this multicomponent reaction. The combination of TosMIC and other isocyanides was also investigated to give the desired products in acceptable yields. The current protocol features use of iron catalyst and nontoxic media, broad substrate scope, mild conditions, and operational simplicity.