Formation of a Unsymmetrical Ring System via C-H Bond Activation of Diazobenzene by Stable N-Heterocyclic Chlorosilylene (PhC(NtBu)2SiCl)

The reaction of N-heterocyclic chlorosilylene (1; LSiCl, L = PhC(NtBu)(2)) with diazobenzene is described, which afforded the unsymmetrical polycyclic product 2 via chlorosilylene mediated aromatic C-H bond activation. The reaction proceeds without the cleavage of the N-N bond of diazobenzene. Polycycle 2 was fully characterized by single-crystal X-ray diffraction analysis, multinuclear NMR spectroscopy, EI-MS spectrometry, and elemental analysis.