Manganese-mediated reductive N,N-dialkylation of nitroarenes: a dramatic NiI2 effect

A practical method for the synthesis of N,N-dialkyl anilines via reductive dialkylation of nitroarenes has been developed. This protocol uses inexpensive substrates, and cheap NiI2 has been identified as the key promoter for the transformation. It features high functional group tolerance and can be applied for the formal synthesis and late-stage modification of drugs or pesticides. Preliminary mechanistic studies imply that aryl hydroxylamine might serve as the intermediate.

Automated summary

A practical method for the synthesis of N,N-dialkyl anilines via reductive dialkylation has been developed using inexpensive substrates and cheap NiI2 as the key promoter. This method demonstrates high functional group tolerance and can be used for the synthesis and modification of drugs or pesticides.