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Issue 2, 2011
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Vinyldisiloxanes: their synthesis, cross coupling and applications

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During the studies towards the development of pentafluorophenyldimethylsilanes as a novel organosilicon cross coupling reagent it was revealed that the active silanolate and the corresponding disiloxane formed rapidly under basic conditions. The discovery that disiloxanes are in equilibrium with the silanolate led to the use of disiloxanes as cross coupling partners under fluoride free conditions. Our previous report focused on the synthesis and base induced cross coupling of aryl substituted vinyldisiloxanes with aryl halides; good yields and selectivities were achieved. As a continuation of our research, studies into the factors which influence the successful outcome of the cross coupling reaction with both alkyl and aryl substituted vinyldisiloxanes were examined and a proposed mechanism discussed. Further investigation into expanding the breadth and diversity of substituted vinyldisiloxanes in cross coupling was explored and applied to the synthesis of unsymmetrical trans-stilbenes and cyclic structures containing the trans-alkene architecture.

Graphical abstract: Vinyldisiloxanes: their synthesis, cross coupling and applications

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The article was received on 28 Jun 2010, accepted on 07 Sep 2010 and first published on 12 Oct 2010

Article type: Paper
DOI: 10.1039/C0OB00338G
Citation: Org. Biomol. Chem., 2011,9, 504-515
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    Vinyldisiloxanes: their synthesis, cross coupling and applications

    H. F. Sore, C. M. Boehner, L. Laraia, P. Logoteta, C. Prestinari, M. Scott, K. Williams, W. R. J. D. Galloway and D. R. Spring, Org. Biomol. Chem., 2011, 9, 504
    DOI: 10.1039/C0OB00338G

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