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Dialkyl 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.
EINECS Number: 212-271-4
Specific Gravity: 0.9969
Flashpoint: 98°C (208°F)
HMIS Key: 2-1-1-X
Hydrolytic Sensitivity: 3: reacts with aqueous base
Refractive Index: 1.5795
Application: Converts amides to aldehydes in combination with Ti(OiPr)4.2
Selective reduction of esters.3
Silylates 1,2-diols in presence of tris(pentafluorophenyl)borane.4
Used in enantioselective reduction of imines.5
Reference: 2. Bower, S. et al. Angew. Chem., Int. Ed. Engl. 1996, 35, 1515.
3. Onta, T. et al. Tetrahedron Lett. 1999, 40, 6963.
4. Blackwell, J. M. et al. J. Org. Chem. 1999, 64, 4887.
5. Takai, I. et al. Organometallics 1999, 18, 2271.
Fieser: F&F: Vol. 1, p 348.