Imine-stabilized silylium ions: synthesis, structure and application in catalysis

Area of Science:

• Organometallic Chemistry
• Catalysis
• Silicon Chemistry

Background:

• Silylium ions are highly reactive silicon species.
• Stabilization of silylium ions is crucial for their study and application.
• Previous studies focused on phosphine-stabilized silylium ions.

Purpose of the Study:

• To synthesize novel norbornene-based imine-stabilized silylium ions.
• To characterize these new silylium ions in solution and solid states.
• To investigate their Lewis acidity and catalytic activity.

Main Methods:

• Synthesis of imine-stabilized silylium ions via reaction of sulfide-stabilized silylium ion with carbonyl derivatives.
• Characterization using NMR spectroscopy and X-ray diffraction.
• Density Functional Theory (DFT) calculations.

Main Results:

• Successful synthesis of novel norbornene-based imine-stabilized silylium ions.
• Comprehensive characterization confirming their structure and properties.
• DFT calculations revealed strong Lewis acid character, unlike related phosphine-stabilized silylium ions.
• Demonstrated ability to activate Si-H bonds and catalyze hydrosilylation.

Conclusions:

• Novel imine-stabilized silylium ions were synthesized and fully characterized.
• These silylium ions possess significant Lewis acidity.
• They serve as effective catalysts for the hydrosilylation of carbonyl derivatives under mild conditions.