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

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 alpha-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.

Automated summary

A Fe(III)-catalyzed N-amidomethylation of secondary and primary anilines with p-toluenesulfonylmethyl isocyanide (TosMIC) in water is described in this study. TosMIC acts as a source of methylene and an amidating reagent, forming alpha-amino amides in a multicomponent reaction. The use of iron catalyst and nontoxic media allows for a broad substrate scope, mild conditions, and operational simplicity.