- Synonyms TRIMETHYLSILYLTRI-n-BUTYLTIN
- HMIS 2-1-1-X
- Molecular Formula C15H36SiSn
- Molecular Weight (g/mol) 363.22
- TSCA No
- Boiling Point (˚C/mmHg) 102-103/0.5
- Density (g/mL) 1.040
- Refractive Index @ 20˚C 1.4880
Review of synthetic utility.1
Undergoes cis addition to terminal acetylenes with Bu3Sn internal.2
Intermediate for 3-substituted cyclobutenone.3
Sn-Si bond shown to react with COD Pt(cod)2 and phosphines to form bis((phosphino)silyl)tinplatinum(ll) complexes, which insert into acetylenes.4
Used in the synthesis of ?-amidotributylstannanes.5
1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 719-723.
2. Chenard, B. et al. J. Org. Chem. 1986, 51, 3561.
3. Liebeskind, L. S. et al. J. Org. Chem. 1994, 59, 7917.
4. Sagawa, T. et al. Organometallics 2003, 22, 4433.
5. >Mita, T.; et al. Synthesis 2012, 194.
Organotin 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.
Tri-n-butylstannyltrimethylsilane; Trimethylsilyltri-n-butyltin; Trimethyl(tributylstannyl)silane
Metal-Organic Chemistry, Articles
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