n-BuLi-promoted nucleophilic addition of unactivated C(sp3)–H bonds to diazo compounds as N-terminal electrophiles: efficient synthesis of hydrazine derivatives

Abstract

A n-BuLi-promoted intermolecular nucleophilic addition of unactivated C(sp³)–H bonds (benzylic carbon atom of alkylazaarenes and α-carbon of thioethers) to diazo compounds as N-terminal electrophiles has been developed. This reaction not only provides an efficient method for electrophilic amination of unactivated C(sp³)–H bonds under transition metal- and oxidant-free conditions, but also provides a simple and efficient strategy for the synthesis of functionalized benzylhydrazines and alkylthio-substituted ethylhydrazines in a single step.