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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.
EINECS Number: 213-919-9
Alternative Name: TRIMETHYLSILYLACETYLENE
Specific Gravity: 0.709
Flashpoint: -26°C (-15°F)
HMIS Key: 2-4-1-X
Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions
Refractive Index: 1.3880
Application: Review of synthetic utility.1
Reacts w/ aryl aldehydes to form diethynylmethane derivatives.10
Useful in the preparation of unsymmetrical diarylacetylenes.11
Ethynylates aromatic compounds.2
Precursor to trimethylsilylethynyl copper reagent.3
Lithiated derivative (n-BuLi treatment) reacts with halotriazines to produce monomers.4
Employed in ortho ethenylation of phenols.5
Undergoes Diels-Alder reactions with butadienes.6
Converts imines to propargyl amines.7
Forms propargylic amines from aldehydes and amines in aqueous system.8
Regioselectively forms either regioisomeric enyne upon addition to propargyl amines depending on catalyst employed.9
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. 569-580.
10. Girard, D. et al. Tetrahedron Lett. 2007, 48, 6022.
11. Mio, M. et al. Org. Lett. 2002, 4, 3199.
2. Austin, W. et al. J. Org. Chem. 1981, 46, 2280.
3. Sakata, H. et al. Tetrahedron Lett. 1987, 28, 5719.
4. Kouveetakis, J. et al. Chem. Mater. 1994, 6, 636.
5. Kobayashi, K.; Yamaguchi, M. Org. Lett. 2001, 3, 241.
6. Paik, S.-J. et al. Org. Lett. 1999, 1, 2045.
7. Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319.
8. Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584.
9. Matsuyama, N. et al. J. Org. Chem. 2009, 74, 3576.
Additional Properties: 310Doped polymer films are conductive