Application
Can be cross-coupled with aryl chlorides.1
Used to acylate aryl triflates.2
Undergoes Stille cross-coupling reactions as employed in the syntheses of three cladiellins.3
Cross-couples with vinyl sulfides.4
Can be cross-coupled with heteroaromatic chlorides.5
Reference
1. Soderquist, J. et al. Tetrahedron Lett. 1983, 24, 2361.
2. Stoltz, B. M. et al. J. Am. Chem. Soc. 2000, 122, 9044.
3. Clark, J. S. et al. Angew. Chem., Int. Ed. Engl. 2010, 49, 9867.
4. Schleiss, J.; Rollin, P.; Tatibouet, P. Angew. Chem., Int. Ed. Engl. 2010, 49, 577.
5. Hong. L. et al. Bioorg. Med. Chem. Lett. 2010, 20, 679.
Safety
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.
1-Ethoxyvinyltri-n-butyltin; Tri-n-butyl(1-ethoxyvinyl)stannane
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
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