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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: 67° / 5
Molecular Weight: 174.32
Specific Gravity: 0.896
Flashpoint: 82°C (180°F)
HMIS Key: 2-2-1-X
Hydrolytic Sensitivity: 1: no significant reaction with aqueous systems
Refractive Index: 1.5284
Application: 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
Reference: 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.