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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: 133-5°
EINECS Number: 238-671-9
Melting Point: 22°
Molecular Weight: 170.40
Specific Gravity: 0.770
Flashpoint: 2°C (36°F)
HMIS Key: 2-4-1-X
Hydrolytic Sensitivity: 2: reacts with aqueous acid
Refractive Index: 1.413
Application: Key review.1
Used to prepare 1,2-bis(aryl)acetylenes.3
Reacts with internal acetylenes to form 1,2,4,5-tetrasubstituted benzenes.4
Useful in silicon-mediated Sonogashira cross-coupling reactions.5
Used to prepare 4-alkynylthiazoles.6
Reference: 1. Weber, W. In Silicon Reagents for Organic Synthesis; Springer-Verlag: 1983, p129.
2. Vollhardt, P. Acc. Chem. Res. 1977, 10, 1.
3. Nishihara, Y. et al. J. Org. Chem. 2000, 65, 1780.
4. Li, S. et al. Org. Lett. 2009, 11, 3318.
5. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011.
6. Arunkukmar, K. et al. Tetrahedron Lett. 2012, 53, 3885.
Additional Properties: Versatile reagent for introducing unsaturation