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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
Boiling Point: 102-3° / 0.5
Molecular Weight: 363.22
Alternative Name: TRIMETHYLSILYLTRI-n-BUTYLTIN
Specific Gravity: 1.040
HMIS Key: 2-1-1-X
Hydrolytic Sensitivity: 1: no significant reaction with aqueous systems
Refractive Index: 1.4880
Application: 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
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. 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.