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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.
Triethylsilane; Triethylsilyl hydride; Triethylsilicon hydride
EINECS Number: 210-535-3
Specific Gravity: 0.7309
Flashpoint: -3°C (27°F)
HMIS Key: 2-4-1-X
Hydrolytic Sensitivity: 3: reacts with aqueous base
Refractive Index: 1.4123
Application: Versatile reducing agent; key reviews.1,2,3,4
Employed in the regioselective reduction of a ketal in the synthesis of Tamiflu.10
Review on organosilane protecting groups.5
Silylates tertiary alcohols in presence of tris(pentafluorophenyl)borane.6
Silylates arenes in presence of Ru catalyst and t-butylethylene.7
Used in reductive cyclization of ynals.8
Readily converted directly to triethylsilyl carboxylates.9
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. 506-514.
10. Federspiel, M. et al. Org. Proc. Res. Dev. 1999, 3, 266.
2. Nagai, Y. Org. Prep. Proc. Int. 1980, 12, 13.
3. F&F: Vol. 1, p 1218; Vol. 2, p 433; Vol. 3, p 304; Vol. 4, p 562; Vol. 6, p 652; Vol. 7, p 387; Vol. 8, p 501; Vol. 9, p 418; Vol. 10, p 483; Vol. 11, p 482; Vol. 15, p 338; Vol. 16, p 356; Vol. 17, p 367.
4. Larson, G. L.; Fry, J. L. Ionic and Organometallic-Catalyzed Organosilane Reductions, Volume 71, Denmark, S. E., Ed. John WIley and Sons, 2008
5. Larson, G. L. “Silicon-Based Blocking Agents” Gelest, Inc. 2014.
6. Blackwell, J. M. et al. J. Org. Chem. 1999, 64, 4887.
7. Ezbiansky, K. et al. J. Organometal. Chem. 1998, 17, 1455.
8. Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc.1999, 121, 6098.
9. Chahan, M. et al. Org. Lett. 2000, 2, 1027.
Additional Properties: 250Dipole moment: 0.75 debyeSurface tension: 20.7 mN/m?Hcomb: -1,272 kcal/mole?Hform: -41 kcal/mole