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Silane 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: 113-4°
EINECS Number: 219-084-7
Molecular Weight: 141.07
Alternative Name: 1,1-DICHLOROSILACYCLOBUTANE
Specific Gravity: 1.201
Flashpoint: 9°C (48°F)
HMIS Key: 3-4-1-X
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
Refractive Index: 1.4620
Application: Reaction with LiN(iPr)2 and CH2X2 provides 1,1-dimethyl-2-halosilacyclopentanes.1
Arylchlorosilyl derivatives used in cross-coupling to biaryls.2
Vinylchlorosilyl derivatives used in cross-coupling to 1,3-butadienes.3
Starting material for spirocyclic organosilanes.4
Reference: 1. Matsumoto, K. Tetrahedron 1993, 49, 8487.
2. Denmark, S. E.; Wu, Z. Org. Lett. 1999, 1, 1495.
3. Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821.
4. Déjean, V. et al. Organometallics 2000, 19, 711.