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- HMIS 2-2-1-X
- Molecular Formula C11H14Si
- Molecular Weight (g/mol) 174.32
- TSCA No
- Boiling Point (˚C/mmHg) 67° / 5
- Density (g/mL) 0.896
- Flash Point (˚C) 82°C (180°F)
- Refractive Index @ 20˚C 1.5284
Reacts with tetraphenylcyclopentadienone to form pentaphenylphenyltrimethylsilane.1
Cross couples with aryl halides and triflates as well as homocouples to 1,2-diynes.2
Undergoes alkynyl cross metathesis reactions.3
Provides the ethynyl silver acetylide.4
Reacts w/ propargyl chlorides to form 1,2-diene-4-ynes.5
Ethynylsilanes react w/ propargyl halides to form 1,4-diynes.6
1. Jianhua, C. et al. In Silicon Chemistry; Corey, J., et al. Ed.; Wiley: 1988: p. 105.
2. Nashihara, Y. et al. J. Org. Chem. 2000, 65, 1780.
3. Furstner, A.; Mathes, C. Org. Lett. 2001, 3, 221.
4. Vitérisi, A. et al. Tetrahedron Lett. 2006, 47, 2779.
5. Montel, F. et al. Org. Lett. 2006, 8, 1905.
6. Kuninobu, Y.; Ishii, E.; Takai, K. Angew. Chem., Int. Ed. Engl. 2007, 46, 3296.
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.
Silicon Chemistry, Articles
Hatanaka and Hiyama first reported the palladium-catalyzed, fluoride-promoted reaction of aryl, alkenyl, allyl, and ethynyltrimethylsilanes with aryl, vinil and allyl halides to form the respective cross-coupled products
In amongst the considerable chemistry of acetylenes there lies some unique chemistry of alkynylsilanes (silylacetylenes) some of which is reviewed herein. This unique character is exemplified not only in the silyl protection of the terminal C–H of acetylenes, but also in the ability of the silyl group to be converted into other functionalities after reaction of the alkynylsilane and to its ability to dictate and improve the regioselectivity of reactions at the triple bond. This, when combined with the possible subsequent transformations of the silyl group, makes their chemistry highly versatile and useful.