Description
Additional Properties
Hydrolytic Sensitivity 8: reacts rapidly with moisture, water, protic solvents Application Review of synthetic utility.1 Reduces ?-hydroxyketones stereoselectively.2 Used in the tethered reactions of unsaturated alcohols.3 Used in the silicon-based cross-coupling of vinyl ethers with aryl iodides.4 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. 151-156. 2. Anwar, S. et al. Chem. Comm. 1986, 831. 3. Robertson, J. et al. Tetrahedron Lett. 1998, 39, 669. 4. Evans, P. A.; Baum, E. W. J. Am. Chem. Soc. 2004, 126, 11150. Safety
Packaging Under Nitrogen Specialty Silicon-Based Blocking Agent Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure. 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. Diisopropylchlorosil
ane; Chlorodiisopropylsil
ane; Chlorobis(1-methylet
hyl)silane
Silylates and reduces β-hydroxy ketones selectively
Reduces β-hydroxyketones stereoselectively
Used in a silylation-reduction
-allylation sequence of β-hydroxy esters to homoallylic-substitu
ted 1,3-diols
Used in the silylation-hydrosila
tion-oxidation of allyl alcohols to 1,3-diols
Reaction carried out in diastereoselective manner
Photochemically removable
Reduces β-hydroxy ketones to anti-1,3 diols
Used in the tethered reactions of unsaturated alcohols
Used in the silicon-based cross-coupling of vinyl ethers with aryl iodides
Extensive review of silicon based reducing agents: Larson, G.; Fry, J. L. "Ionic and Organometallic-Catal
yzed Organosilane Reductions", Wipf, P., Ed.; Wiley, 2007
Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure
