Vinyldisiloxanes: their synthesis, cross coupling and applications

Hannah F. Sore, Christine M. Boehner, Luca Laraia, Patrizia Logoteta, Cora Prestinari, Matthew Scott, Katharine Williams, Warren R. J. D. Galloway, David R. Spring

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

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.
Original languageEnglish
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number2
Pages (from-to)504-515
ISSN1477-0520
DOIs
Publication statusPublished - 2011
Externally publishedYes

Cite this

Sore, H. F., Boehner, C. M., Laraia, L., Logoteta, P., Prestinari, C., Scott, M., Williams, K., Galloway, W. R. J. D., & Spring, D. R. (2011). Vinyldisiloxanes: their synthesis, cross coupling and applications. Organic and Biomolecular Chemistry, 9(2), 504-515. https://doi.org/10.1039/c0ob00338g