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The reaction of N-heterocyclic chlorosilylene (1; LSiCl, L = PhC(NtBu)2) with diazobenzene is described, which afforded the unsymmetrical polycyclic product 2 via chloro-silylene 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.

organometallics

Formation of a Unsymmetrical Ring System via C–H Bond Activation of Diazobenzene by Stable N-Heterocyclic Chlorosilylene (PhC(N<i>t</i>Bu)<sub>2</sub>SiCl)

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

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