Synthesis of benzyl hydrazine derivatives via amination of benzylic C(sp3)–H bonds with dialkyl azodicarboxylates

Abstract

A novel synthesis of benzyl hydrazines through oxidative amination of benzylic C–H bonds has been developed. The resulting aminated products are accessed directly from the reaction of alkylarenes with dialkyl/diphenyl azodicarboxylates using Cu₂O/Phen as the catalytic system. The reaction proceeded smoothly and a decent range of N-substituted hydrazides was synthesized in acceptable to good yields. Both primary and secondary sp³ C–H sources afford only monoamination products.