tBuLi-Promoted Intermolecular Regioselective Nucleophilic Addition of Arenes to Diazo Compounds as N-Terminal Electrophiles: Efficient Synthesis of Hydrazine Derivatives

The tBuLi-promoted intermolecular direct nucleophilic addition of arenes to diazo compounds as the N-terminal electrophiles has been developed. This reaction proceeds in a completely regioselective manner and is an efficient method for the preparation of hydrazine derivatives in high to excellent yields. This transformation not only provides an efficient approach for aromatic C-N bond formation under transition-metal-free and oxidant-free conditions but also represents a strategy for the 3-amination of pyridines and the dearomatization of indoles.