Fast Synthesis of Hydrazine and Azo Derivatives by Oxidation of Rare-Earth-Metal-Nitrogen Bonds

A novel N-N coupling reaction was developed through the oxidation of rare-earth-metal-nitrogen bonds produced by treatment of the easily available rare-earth-metal amides [(Me3Si)(2)N](3)RE(mu-Cl)Li(THF)(3) with aromatic primary or secondary amines. The reaction provides the symmetrical or unsymmetrical azo compounds and hydrazine derivatives in good to high yields within a very short time under mild conditions.