| Reducing Agent | Structure | Comments |
|---|---|---|
| SIT8330.0 Triethylsilane [617-86-7] TSCA |  | Used to reduce metal salts.85 Enhances deprotection of t-butoxycarbonyl-protected amines and tert-butyl esters.86 Used in the reductive amidation of oxazolidinones with amino acids to provide dipeptides.87 Converts aldehydes to symmetrical and unsymmetrical ethers.88 Used in the ‘in-situ’ preparation of diborane and haloboranes.89 |
| SIT8570.0 Trimethylsilane [993-07-7] TSCA |  | Potential reducing agent that will produce low boiling hexamethyldisiloxane by-product. |
| SIT8385.0 Triisopropylsilane [6485-79-6] |  | Very sterically-hindered silane. Used as a cation scavenger in the deprotection of peptides.90 |
| SIT8665.0 Triphenylsilane [789-25-3] TSCA |  | More effective radical-based reagent for reduction of organic halides than the trialkylsilanes.88 Compares well with tri-n-butyltin hydride in reduction of enones to ketones.63 Shows good selectivity in the reduction of cyclic hemiacetals.77 Converts O-acetyl furanoses and pyranoses to deoxy sugars.91 |
| SIT8709.0 Tri-n-propylsilane [998-29-8] TSCA |  | Reactivity similar to that of triethylsilane. |
| SIT8376.0 Tri-n-hexylsilane [2929-52-4] TSCA |  | Reactivity similar to that of triethylsilane, but has higher boiling point and produces a higher boiling by-product. |
| SIT8185.0 Triethoxysilane [998-30-1] TSCA |  | Reduces esters in the presence of zinc hydride catalyst.52 Reduces aldehydes and ketones to alcohols via the silyl ethers in presence of fluoride ion.92 Gives 1,2 reduction of enones to allyl alcohols.93 |
| SIT8721.0 Tris(trimethylsiloxy)silane [1873-89-8] |  | Gives highly stereoselective reduction of substituted cyclohexanones.51 |
| SIT8724.0 Tris(trimethylsilyl)silane [1873-77-4] |  | Undergoes exothermic decomposition at >100 °C. Radical-based reducing agent for organic halides selenides, xanthates and isocyanides and ketones in high yields.20 Can provide complementary stereoselectivity to tri-n-butyltin hydride in the reduction of gem dihalides.94 Mild reducing agent in nucleoside chemistry.95 |
| SID3258.0 Di-tert-butylmethylsilane [56310-20-4] |  | Used in reductive trifluoroacetolysis of ketones. Reacts faster than di-tert-butylsilane.72 |
| SID3410.0 Diethylmethylsilane [760-32-7] TSCA |  | Similar to triethylsilane with lower boiling point. |
| SID3535.0 Diisopropylchlorosilane [2227-29-4] TSCA |  | Used in a silylation-reduction-allylation sequence of β-hydroxy esters to homoallylic-substituted 1,3-diols.96 Used in the silylation-hydrosilation-oxidation of allyl alcohols to 1,3-diols.97 Reaction carried out in diastereoselective manner. Reduces β-hydroxy ketones to anti-1,3 diols.98 |
| SID4070.0 Dimethylchlorosilane [1066-35-9] TSCA |  | Will form high-boiling polymeric by-products with aqueous work-up. |
| SID4125.0 Dimethylethoxysilane [14857-34-2] TSCA |  | Will form high-boiling polymeric by-products with aqueous work-up. |
| SID4555.0 Diphenylmethylsilane [776-76-1] TSCA |  | Used to reduce α-alkoxy ketones to diols and α-amino ketones to aminoethanols with high stereoselectivity.99 |
| SIE4894.0 Ethyldimethylsilane [758-21-4] TSCA |  | Similar to triethylsilane with lower boiling point. |
| SIE4890.0 Ethyldichlorosilane [1789-58-8] TSCA |  | Will form high-boiling polymeric by-products with aqueous work-up. |
| SIM6504.0 Methyldichlorosilane [75-54-7] TSCA |  | Provides better diastereoselective reductive aldol reaction between an aldehyde and an acrylate ester than other silanes.100 Forms high-boiling polymeric by-products upon aqueous work-up. |
| SIM6506.0 Methyldiethoxysilane [2031-62-1] TSCA |  | Will form high-boiling polymeric by-products with aqueous work-up. |
| SIO6619.0 Octadecyldimethylsilane [32395-58-7] |  | Similar to triethylsilane with much higher boiling point. |
| SIP6729.0 Phenyldimethylsilane [766-77-8] TSCA |  | Used to reduce α-amino ketones to aminoethanols with high stereoselectivity.99 Used in the fluoride ion-catalyzed reduction of aldehydes and ketones, and α-substituted alkanones to threo products.42 Erythro reduction of α-substituted alkanones to diols and aminoethanols.101 Together with CuCl reduces aryl ketones, but not dialkyl ketones.102 Used in the silylformylation of acetylenes.103 Excellent reducing agent for the reduction of enones to saturated ketones.104 Shows better selectivity than LAH in the reduction of oximes to alkoxyamines.57 |
| SIP6737.0 Phenylmethylchlorosilane [1631-82-9] TSCA |  | Will form high-boiling polymeric by-products with aqueous work-up. |
| SIT7544.0 1,1,4,4-tetramethyldisilethylene [20152-11-8] |  | Contains two available hydrides for reduction. Has potential for stereoselective reduction of dicarbonyls. |
| SIT8155.0 Trichlorosilane [10025-78-2] TSCA |  | Will form high-boiling polymeric by-products with aqueous work-up. Reduces aromatic carbonyl systems to give benzyltrichlorosilanes, which can be desilylated to toluenes.105-107 Reduces phosphine oxides to phosphines.108 |
| Reducing Agent | Structure | Comments |
|---|---|---|
| SIT4230.0 Dimethylsilane [1111-74-6] TSCA |  | Very low boiling point silane that is a gas at atmospheric conditions. |
| SID3342.0 Di-tert-butylsilane [30736-07-3] |  | Sterically-hindered silane reducing agent. |
| SID3368.0 Dichlorosilane [4109-96-0] TSCA |  | Gives improved yields in reduction of imines over that of trichlorosilane.56 |
| SIB3368.2 Dichlorosilane, 25% in xylene [4109-96-0] TSCA | | Easier to handle form of dichlorosilane. |
| SID3415.0 Diethylsilane [542-91-6] TSCA |  | Used in the ‘in-situ’ preparation of diborane and haloboranes.89 |
| SID4559.0 Diphenylsilane [775-12-2] TSCA |  | Used in the preparation of silyl-substituted alkylidene complexes of tantalum.109 Used in the ionic reduction of enones to saturated ketones.110 Used in the reductive cyclization of unsaturated ketones.111,112 Reduces esters in the presence of zinc hydride catalyst.53 Reduces α-halo ketones in presence of Mo(0).113 Reduces thio esters to ethers.22 Reduces esters to alcohols with Rh catalysis.49 Employed in the asymmetric reduction of methyl ketones114 and other ketones115,116. Reductively cleaves allyl acetates.117 |
| SIP6742.0 Phenylmethylsilane [766-08-5] TSCA |  | Used in the preparation of silyl-substituted alkylidene complexes of tantalum.109 |
| Reducing Agent | Structure | Comments |
|---|---|---|
| SIH6166.2 n-Hexylsilane [1072-14-6] TSCA |  | |
| SIO6635.0 n-Octadecylsilane [18623-11-5] TSCA |  | |
| SIO6712.5 n-Octylsilane [871-92-1] TSCA |  | |
| SIP6750.0 Phenylsilane [694-53-1] TSCA |  | Employed in the reduction of esters to ethers.118 Reduces α,β-unsaturated ketones to saturated ketones in the presence of tri-n-butyltin hydride.119 Reduces tin amides to tin hydrides.120 Used in the tin-catalyzed reduction of nitroalkanes to alkanes.121 Reduces α-halo ketones in presence of Mo(0).113 |
| Reducing Agent | Structure | Comments |
|---|---|---|
| SIO6696.5 Octakis(dimethylsiloxy)-T8-silsesquioxane [125756-69-6] |  | Solid siloxane reducing agent. Offers 8 Si-H bonds. Potential for easy removal of silicon byproducts. |
| SIH6117.0 1,1,3,3,5,5-hexamethyltrisiloxane [1189-93-1] TSCA |  | High molecular weight silane reducing agent. |
| SIP6718.0 Pentamethylcyclopentasiloxane, 90% [6166-86-5] TSCA |  | |
| SIH5844.0 Heptamethyltrisiloxane [2895-07-0] |  | |
| SIP6736.5 Phenylhydrocyclosiloxanes, contains linears |  | High-boiling siloxane reducing agent. |
| SIP6826.0 Phenyltris(dimethylsiloxy)silane, 95% [18027-45-7] TSCA |  | High molecular weight silane reducing agent. |
| SIT7274.0 1,1,3,3-tetraisopropyldisiloxane [18043-71-5] |  | Sterically-hindered silane reducing agent with potential for diastereoselective reductions. |
| SIT7278.0 Tetrakis(dimethylsiloxy)silane [17082-47-2] TSCA |  | High molecular weight silane reducing agent. |
| SIT7530.0 1,3,5,7-tetramethylcyclo-tetrasiloxane [2370-88-9] TSCA |  | High molecular weight silane reducing agent. |
| SIT7546.0 1,1,3,3-tetramethyldisiloxane [30110-74-8] TSCA |  | Reduces aromatic aldehydes to benzyl halides.38 Used in the reductive halogenation of aldehydes and epoxides.122 |
| SIT8721.0 Tris(trimethylsiloxy)silane [1873-89-8] |  | High molecular weight silane reducing agent. |
| HMS-013 through HMS-501 having various MW’s, viscosities, and hydride content. Methylhydrosiloxane-dimethylsiloxane copolymers [68037-59-2] TSCA |  | Potential reducing agents in the mode of HMS-991 or HMS-992. |
| HMS-991 or HMS-992 Polymethylhydrosiloxane [63148-57-2] TSCA |  | Reduces lactones to lactols.55 Reduces aldehydes, ketones, esters, lactones, triglycerides and epoxides to alcohols with zinc hydride catalysis.52 With titanium tetraisopropoxide catalysis carries out reductive amination of ketones and aldehydes82 and the reduction of acids or esters to 1° alcohols.50 With TBAF catalysis selectively reduces aldehydes over ketones.43 Used to generate tri-n-butyltin hydride ‘in-situ’ and in a one-pot hydrostannylation/Stille coupling sequence.123 Reduces esters to alcohols.54 |
| Reducing Agent | Structure | Comments |
|---|---|---|
| SNT8130 Tri-n-butyltin hydride [688-73-3] TSCA |  | Has been reviewed.80 Catalyzes the Si-H reduction of α,β-unsaturated ketones.119 Useful in the reductive amination of ketones and aldehydes to form 3° amines.81 |
| GET8100 Tri-n-butylgermane [998-39-0] |  | Reduces acid chlorides to aldehydes in presence of Pd(0).83 Effects free-radical reductive addition of alkyl halides to olefins.124 Reduces benzylic chlorides 70x faster than silyl hydrides.125 |
| GET8660 Triphenylgermane [2816-43-5] |  | Readily adds to terminal acetylenes and olefins.126 Used in the reductive alkylation of acrylonitrile and enones.84 |
| GET8560 Trimethylgermane [1449-63-4] |  | Effects halogen displacement of alkyl halides with hydrogen when exposed to UV.127 |