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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.
Boiling Point: 55-7° / 80
EINECS Number: 237-195-9
Molecular Weight: 179.13
Specific Gravity: 1.163
Flashpoint: 15°C (59°F)
HMIS Key: 2-4-1-X
Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions
Refractive Index: 1.4580
Application: Review of synthetic utility.1
Starting material for preparation of ?-trimethylsilylvinylketone.2
Starting material for preparation of trisubstituted olefins.3
Potential for cross-coupling protocols to yield ?-substituted vinylsilanes.4
Reacts with dichlorocarbene followed by fluoride-promoted elimination to formcyclopropenes.5
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. 109-110.
2. Stork, G. et al. J. Am. Chem. Soc. 1973, 95, 6152.
3. Miller, R. et al. J. Org. Chem. 1979, 44, 4623.
4. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011.
5. Billups, W. E. et al. Tetrahedron Lett. 1984, 25, 3935.
Fieser: F&F: Vol. 7, p 193; Vol. 8, p 56, p 515; Vol. 9, p 56; Vol. 10, p 442; Vol. 11, p 286.
Additional Properties: Employed in cyclopentene annulations