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Alkynylsilane 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: 136°
Molecular Weight: 140.30
Alternative Name: TRIETHYLSILYLACETYLENE
Specific Gravity: 0.783
Flashpoint: 17°C (63°F)
HMIS Key: 2-4-1-X
Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions
Refractive Index: 1.4430
Application: Reacts with enol silyl ethers to form ?,?-bis-trans-?-triethylsilylethenyl ketones.1
Useful in Sonogashira cross-coupling reactions w/ more stable silyl group than the trimethylsilyl group.2
Reference: 1. Amemiya, R. et al. Tetrahedron Lett. 2006, 47, 1797.
2. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011.