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Updated: Mar 24, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Hydrosilylation in Aryliminopyrrolide-Substituted Silanes
Léon Witteman1, Tim Evers1, Zhan Shu1
1Department of Chemistry, Debye Institute for Nanomaterials Science, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht, The Netherlands.
Abstract:
A range of silanes was synthesized by the reaction of HSiCl3 with iminopyrrole derivatives in the presence of NEt3 . In certain cases, intramolecular hydrosilylation converts the imine ligand into an amino substituent. This reaction is inhibited by factors such as electron-donating substitution on Si and steric bulk. The monosubstituted ((Dipp) IMP)SiHMeCl ((Dipp) IMP=2-[N-(2,6-diisopropylphenyl)iminomethyl]pyrrolide), is stable towards hydrosilylation, but slow hydrosilylation is observed for ((Dipp) IMP)SiHCl2 . Reaction of two equivalents of (Dipp) IMPH with HSiCl3 results in the hydrosilylation product ((Dipp) AMP)((Dipp) IMP)SiCl ((Dipp) AMP=2-[N-(2,6-diisopropylphenyl)aminomethylene]pyrrolide), but the trisubsitituted ((Dipp) IMP)3 SiH is stable. Monitoring the hydrosilylation reaction of ((Dipp) IMP)SiHCl2 reveals a reactive pathway involving ligand redistribution reactions to form the disubstituted ((Dipp) AMP)((Dipp) IMP)SiCl as an intermediate. The reaction is strongly accelerated in the presence of chloride anions.
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