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Fluoride-free cross coupling using vinyldisiloxanes.

Hannah F Sore1, Christine M Boehner, Simon J F MacDonald

  • 1Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK CB2 1EW.

Organic & Biomolecular Chemistry
|March 6, 2009
PubMed
Summary
This summary is machine-generated.

Vinyldisiloxanes can be converted to silanolates under basic conditions. These intermediates then participate in palladium-catalyzed cross-coupling reactions with aryl and heteroaryl halides.

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Area of Science:

  • Organosilicon Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Vinyldisiloxanes are versatile silicon-containing compounds.
  • Palladium-catalyzed cross-coupling reactions are fundamental in organic synthesis.
  • Efficient methods for functionalizing silicon compounds are of significant interest.

Purpose of the Study:

  • To investigate the base-catalyzed equilibration of vinyldisiloxanes.
  • To explore the subsequent palladium-catalyzed cross-coupling of the resulting silanolates.
  • To develop a novel synthetic route for incorporating aryl/heteroaryl groups onto silicon.

Main Methods:

  • Treatment of vinyldisiloxanes with a base to form silanolates.
  • Palladium-catalyzed cross-coupling reactions using aryl/heteroaryl iodides and bromides.
  • Characterization of the resulting products using spectroscopic techniques.

Main Results:

  • Vinyldisiloxanes successfully equilibrate to silanolates under basic conditions.
  • The generated silanolates undergo efficient palladium-catalyzed cross-coupling with various aryl/heteroaryl iodides and bromides.
  • The reaction provides a new method for C-Si bond formation.

Conclusions:

  • A novel synthetic methodology has been established for the functionalization of vinyldisiloxanes.
  • This approach offers a valuable tool for constructing silicon-containing organic molecules.
  • The developed method highlights the utility of silanolates in cross-coupling chemistry.