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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: 88° / 0.1
Molecular Weight: 228.45
Specific Gravity: 0.877
HMIS Key: 2-2-0-X
Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions
Refractive Index: 1.4640
Application: Undergoes Pd-catalyzed cross-coupling with activated aromatic iodides.1
Stable silanol for cross-coupling vinylations.2,3,4
Vinyl silanols cross-couple w/ aryl triflates and nonaflates.5
Potassium salts of silanols cross-couple in absence of fluoride.6
Reference: 1. Denmark, S. et al. Org. Syn. 2005, 81, 42.
2. Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2001, 123, 6439.
3. Denmark, S. E.; Pan, W. J. Organomet. Chem. 2002, 653, 98.
4. Denmark, S. E.; Wehrli, D. Org. Lett. 2000, 2, 565.
5. Denmark, S. E.; Sweis, R. F. Org. Lett. 2002, 4, 3771.
6. Denmark, S. E.; Kallemeyn, J. M. J. Am. Chem. Soc. 2006, 128, 15958.