Description
Additional Properties
Hydrolytic Sensitivity 1: no significant reaction with aqueous systems Application Reviewed.1 Intermediate for vinyllithium by exchange with phenyllithium.2 With CO forms divinyl ketones on reaction with vinyl iodides.3 Reacts with IC6H4CHO in DMF with PdCl2(CH3CN)2 to yield CH2=CHC6H4CHO.4 Reacts with halopyrimidines to yield vinylpyrimidines.5 Employed in one-pot synthesis of pyrroles.6 Reference 1. Scott, W. J.; Moretto, A. F. in Encyclopedia of Reagents for Organic Synthesis 1995, Volume 8, 5503-5506. 2. Seyferth, D. et al. J. Am. Chem. Soc. 1961, 83, 3583. 3. Goure, W. et al. F&F: Vol. 12, p 45; J. Am. Chem. Soc. 1984, 106, 6417. 4. Bumagin, N. Chem. Abstr. 111, 214179; Metal Org. Chem. 1989, 2, 475. 5. Kondo, Y. et al. Chem. Pharm. Bull. 1989, 37, 2814. 6. Nakamura, M. et al. Org. Lett. 1999, 1, 1505. Safety
Packaging Under Nitrogen 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. Vinyltri-n-butyltin; Tributylethenylstann
ane; Tributylvinylstannan
e
Copolymerization parameters - e,Q: 0.800, 0.024
Stille Coupling vinylation reagent
Intermediate for vinyllithium by exchange with phenyllithium
With CO forms divinyl ketones on reaction with vinyl iodides
Reacts with IC6H4CHO in DMF with PdCl2(CH3CN)2 to yield CH2=CHC6H4CHO
Reacts with halopyrimidines to yield vinylpyrimidines
Employed in one-pot synthesis of pyrroles
Extensive review of silicon based cross-coupling agents: Denmark, S. E. et al. "Organic Reactions, Volume 75" Denmark, S. E. ed., John Wiley and Sons, 233, 2011
