Nickel Nanoparticles Catalyzed Cross-Coupling of Diazo Compounds with <i>O</i> -Benzoyl Hydroxylamines

Nickel nanoparticle-catalyzed cross-coupling of diazo compounds with <i>O</i>-benzoyl hydroxylamines via a nickel carbene intermediate was disclosed in this work. A nickel nanoparticle catalyst was generated <i>in situ</i> to decompose diazo compounds to afford organonickel species via migratory insertion of nickel carbene intermediates. The silane not only served as a reductant to produce nickel nanoparticles but also provided hydride to facilitate the cross-coupling reaction. This nickel nanoparticle-catalyzed process exhibited distinct reactivities compared with a homogeneous process.