Vinyldisiloxanes: their synthesis, cross coupling and applications

Area of Science:

• Organosilicon Chemistry
• Organic Synthesis
• Cross-Coupling Reactions

Background:

• Pentafluorophenyldimethylsilanes were investigated as novel organosilicon cross-coupling reagents.
• Rapid formation of active silanolate and disiloxane under basic conditions was observed.
• Disiloxanes were identified as key intermediates in equilibrium with silanolates.

Purpose of the Study:

• To investigate factors influencing cross-coupling reactions using alkyl and aryl substituted vinyldisiloxanes.
• To propose a mechanism for the observed cross-coupling reactions.
• To expand the scope of vinyldisiloxane cross-coupling for synthesizing complex organic structures.

Main Methods:

• Exploration of reaction conditions for base-induced cross-coupling of vinyldisiloxanes with aryl halides.
• Systematic examination of factors affecting cross-coupling efficiency with diverse vinyldisiloxanes.
• Application of developed methods to synthesize unsymmetrical trans-stilbenes and cyclic compounds.

Main Results:

• Established disiloxanes as effective cross-coupling partners under fluoride-free conditions.
• Identified key factors influencing the success of cross-coupling reactions with various vinyldisiloxanes.
• Achieved good yields and selectivities in the synthesis of target molecules.

Conclusions:

• Vinyldisiloxanes are versatile reagents for organosilicon cross-coupling.
• The study provides insights into reaction mechanisms and optimization strategies.
• Developed methodology enables efficient synthesis of valuable organic compounds, including unsymmetrical trans-stilbenes and cyclic architectures.