Reductive alkylation of azoarenes to N-alkylated hydrazines enabled by hexafluoroisopropanol†

Abstract

A one-pot tandem approach to N-alkyl-N,N′-diarylhydrazines was developed using a sequence of reduction of azoarene to hydrazoarene followed by reductive alkylation by an aldehyde. The mild reaction conditions suppress N–N cleaved products and selectively provide trisubstituted hydrazine derivatives. The mechanistic study demonstrates that the iminium formation step is likely to be the rate-limiting step.