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Alkenylsilane Cross-Coupling Agent
The cross-coupling reaction is a highly useful methodology for the formation of carbon-carbon bonds. It involves two reagents, with one typically being a suitable organometallic reagent - the nucleophile - and the other a suitable organic substrate, normally an unsaturated halide, tosylate or similar - the electrophile.
1,3,5,7-Tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane; Methylvinylcyclosiloxane; Tetramethyltetravinylcyclotetrasiloxane; Tetramethyltetraethenylcyclotetrasiloxane
Boiling Point: 110° / 10
EINECS Number: 219-863-1
Melting Point: -43°
Molecular Weight: 344.66
Specific Gravity: 0.998
Flashpoint: 112°C (234°F)
HMIS Key: 2-1-0-X
Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions
Refractive Index: 1.4342
Application: Review of synthetic utility.1
Modifier for Pt-catalyst in 2-component RTVs.2
Core molecule for dendrimers.3
Excellent and inexpensive reagent for vinylations in cross-coupling reactions for the formation of styrenes and dienes.4,5,6
Extensive review on the use in silicon-based cross-coupling reactions.7
Reference: 1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 484-487.
2. Kim, C. et al. Bull. Kor. Chem. Soc. 1997, 18, 164.
3. Broadbridge, R. et al. J. Chem. Soc., Chem. Commun. 1998, 1449.
4. Denmark, S. E.; Butler, C. R. Org. Lett. 2006, 8, 63.
5. Denmark, S. E.; Wang, Z. J. Organomet. Chem. 2001, 624, 372.
6. Denmark, S. E.; Wehrli, D. Org. Lett. 2000, 2, 565.
7. Denmark, S. E. et al. Organic Reactions, Vol. 75, Denmark, S. E. ed., John Wiley and Sons, 233, 2011.
Additional Properties: Undergoes ring-opening polymerization