Description
Additional Properties
Hydrolytic Sensitivity 8: reacts rapidly with moisture, water, protic solvents Application Reviews.1,2 Efficient mediator in organic radical reactions.3 Initiates addition of alkyl iodides to activated olefins.4 Initiates and promotes the radical addition of perfluoroalkyl iodides to olefins in water.5 Hydrosilylates olefins in aqueous systems in presence of azo initiators.6 Reacts with MeLi to form tris(trimethylsilyl)
methyllithium.7 Reacts with LiOMe to form bis(trimethylsilyl)m
ethyllithium.8 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. 747-754. 2. Chatgilialoglu, C. Chem. Eur. J. 2008, 14, 2310. 3. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188. 4. Kishimoto, Y.; Ikariya, T. J. Org. Chem. 2000, 65, 7656. 5. Barata-Vallejo, S.; Postigo, A. J. Org. Chem. 2010, 75, 6141. 6. Postigo, A. et al. Organometallics 2009, 28, 3282. 7. Cook, M. A. et al. J. Organomet. Chem. 1970, 24, 529. 8. Sakurai, H. et al. Tetrahedron Lett. 1973, 4193. Safety
Packaging Under Nitrogen
Store Cold Tri-substituted Silane Reducing Agent Organosilanes are hydrocarbon-like and possess the ability to serve as both ionic and free-radical reducing agents. These reagents and their reaction by-products are safer and more easily handled and disposed than many other reducing agents. The metallic nature of silicon and its low electronegativity relative to hydrogen lead to polarization of the Si-H bond yielding a hydridic hydrogen and a milder reducing agent compared to aluminum-, boron-, and other metal-based hydrides. A summary of some key silane reductions are presented in Table 1 of the Silicon-Based Reducing Agents brochure. Tris(trimethylsilyl)
silane; 1,1,1,3,3,3-Hexameth
yl-2-trimethylsilylt
risilane; TTMS
Oxidizes slowly in contact with air at room temperature
Efficient mediator in organic radical reactions
Initiates addition of alkyl iodides to activated olefins
Initiates and promotes the radical addition of perfluoroalkyl iodides to olefins in water
Hydrosilylates olefins in aqueous systems in presence of azo initiators
Undergoes exothermic decomposition at >100 °C
Radical-based reducing agent for organic halides selenides, xanthates and isocyanides and ketones in high yields
Can provide complementary stereoselectivity to tri-n-butyltin hydride in the reduction of gem dihalides
Mild reducing agent in nucleoside chemistry
Extensive review of silicon based reducing agents: Larson, G.; Fry, J. L. "Ionic and Organometallic-Catal
yzed Organosilane Reductions", Wipf, P., Ed.; Wiley, 2007
