Journal
ACS CATALYSIS
Volume 11, Issue 21, Pages 13085-13090Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c03824
Keywords
C-H silylation; diazene; metalation; homogeneous catalysis; rearrangement
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Funding
- Sorbonne Universite
- CNRS
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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.
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.
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