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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.
Vinyltrimethylsilane; Ethenyltrimethylsilane; Trimethylsilylethene; Trimethylvinylsilane
EINECS Number: 212-042-9
Specific Gravity: 0.6903
Flashpoint: -20°C (-4°F)
HMIS Key: 2-4-0-X
Hydrolytic Sensitivity: 1: no significant reaction with aqueous systems
Refractive Index: 1.3910
Application: Review of synthetic utility.1
Polymerization catalyzed by alkyllithium compounds.2,3,4
Synthetic reactions of vinylsilanes reviewed.5,6
Undergoes Heck coupling to (E)-?-substituted vinyltrimethylsilanes, which can be cross-coupled further.7
Reacts w/ azides to form trimethylsilyl-substituted aziridines.8
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. 755-761.
2. Oku, J. et al. Polymer J. 1991, 23, 1377; Macromolecules 1992, 25, 2780.
3. Gan, Y. et al. Macromolecules 1996, 29, 8285.
4. Rickle, G. J. Macromol. Sci. 1987, A24, 93.
5. Hudrlik, P. In New Applications of Organometallic Reagents in Organic Synthesis; Seyferth, D., Ed.; Elsevier: 1976.
6. F&F: Vol. 5, p 375; Vol. 6, p 637.
7. Jeffery, T. Tetrahedron Lett. 1999, 40, 1673.
8. Bassindale, A. R. et al. J. Chem. Soc., Perkin Trans. 1 2000, 1173.
Fieser: F&F: Vol. 9, p 498; Vol. 10, p 44; Vol. 11, p 41; Vol. 12, p 566.
Additional Properties: 295?Hcomb: 987.3 kcal/mole?Hfus: 7.7 kJ/moleForms polymers which can be fabricated into oxygen enrichment membranes