Transition-Metal-Free Silylation of Unactivated C(sp2)-H Bonds with tert-Butyl-Substituted Silyldiazenes

Aromatic organosilanes bearing C(sp(2))-Si bonds have found increasing applications across the chemical science, yet are mostly produced by atom-uneconomical stoichiometric procedures. Catalytic alternatives using hydrosilanes as silicon sources have also been described, but they display unfavorable thermodynamics and are mostly based on expensive catalytic systems, often derived from noble metals, or lack generality. Herein, we describe the use of an alternative silicon source, namely the tert-butyl-substituted silyldiazenes (tBu-N=N-SiR3), that are readily accessible from commercially available precursors and whose structure enables the C(sp(2))-H bond silylation of unactivated heteroaryl and aryl compounds under ambient, transition-metal-free catalytic conditions.

Automated summary

The study introduces a method for C(sp(2))-H bond silylation using an alternative silicon source that is readily accessible from commercially available precursors, without the need for expensive catalytic systems and noble metal catalysts, showing good generality.