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

Abstract

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.