98264-23-4

Upstream product

• 766-77-8 Dimethylphenylsilane 
• 100-49-2 cyclohexylmethyl alcohol 
• 2043-61-0 cyclohexanecarbaldehyde 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 1432-39-9 dimethyl-p-tolylsilane 
• 454-57-9 fluorodimethylphenylsilane 

Downstream Products

• 100-49-2 cyclohexylmethyl alcohol 

Relevant academic research and scientific papers

Efficient hydrosilylation of carbonyl compounds by 1,1,3,3-tetramethyldisiloxane catalyzed by Au/TiO2

1,1,3,3-Tetramethyldisiloxane (TMDS) is a highly reactive reducing reagent in the Au/TiO2-catalyzed hydrosilylation of carbonyl compounds relative to monohydrosilanes. The reduction of aldehydes or ketones with TMDS can be performed on many occasions at ambient conditions within short reaction times and at low loading levels of gold, whereas typical monohydrosilanes require excess heating and prolonged time for completion. The product yields are excellent, while almost stoichiometric amounts of carbonyl compounds and TMDS can be used. It is postulated that the enhanced reactivity of TMDS is attributed to the formation of a gold dihydride intermediate. This intermediate is also supported by the fact that double hydrosilylation of carbonyl compounds by TMDS is a negligible pathway.

Efficient hydrosilylation of carbonyl compounds by 1,1,3,3-tetramethyldisiloxane catalyzed by Au/TiO2

1,1,3,3-Tetramethyldisiloxane (TMDS) is a highly reactive reducing reagent in the Au/TiO2-catalyzed hydrosilylation of carbonyl compounds relative to monohydrosilanes. The reduction of aldehydes or ketones with TMDS can be performed on many occ

Homobimetallic rhodium NHC complexes as versatile catalysts for hydrosilylation of a multitude of substrates in the presence of ambient air

Two recently reported air- and water-stable di-Rh complexes based on 1,3-bis(3′-butylbenzimidazol-2′-ylidene)benzene were utilized as catalysts for hydrosilylation. Among the substrates investigated were aldehydes, ketones, α,β-unsaturated carbonyls, acyl chlorides, nitriles, alkenes, nitro groups, isocyanates, and tertiary amides. Additionally, carbon dioxide underwent hydrosilylation to produce dimethylphenylsilylformate. The catalysts compared well to other previously reported hydrosilylation catalysts, and the Rh-Cl catalyst was found to be faster and more selective than the Rh-I complex in each case.

First gold complex-catalysed selective hydrosilylation of organic compounds

The first examples of the hydrosilylation of organic compounds such as aldehydes and an aldimine using a catalytic amount of a gold complex, which accomplished versatile regio- and chemo-selective reduction of carbonyl compounds, are described.

Fluoride Ion Catalyzed Reduction of Aldehydes and Ketones with Hydrosilanes. Synthetic and Mechanistic Aspects and an Application to the Threo-Directed Reduction of α-Substituted Alkanones

Reduction of aldehydes and ketones with hydrosilanes proceeded in the presence of a catalytic amount of tetrabutylammonium fluoride or tris(diethylamino)sulfonium difluorotrimethylsilicate in aprotic polar solvents under mild conditions.A significant isotope effect (kH/kD = 1.50) was observed in competitive reduction of acetophenone with HSiMe2Ph and DSiMe2Ph.The reaction was of first order in the concentration of an aprotic polar solvent HMPA.Reduction of 2-methylcyclohexanone gave cis-2-methylcyclohexanol with selectivities up to 95percent.The kinetic and stereochemical results suggest that a hexavalent fluorosilicate - is involved. α-Alkoxy (acyloxy or dimethylamino) ketones were transformed to threo alcohols in high diastereoselectivities.The reduction was also applied to α-methyl-β-keto amides, RCOCH(MeCONR)2, to afford the corresponding threo alcohols in >98percent selectivity.The threo selectivity is explained in terms of the Felkin-Anh model in which interaction of carbonyl oxygen with a countercation is ideally suppressed.The threo-directed reduction was applied to (R)-1-phenyl-4-(2-tetrahydropyranyloxy)-1-penten-3-one and N-(2-benzoylpropanoyl)piperidine.The resulting threo alcohols were respectively converted into (2R,3S)-2,3-(cyclohexylidenedioxy)butanal, a key intermediate of daunosamine synthesis, and into a pharmacologically useful compound threo-N-(3-hydroxy-2-methyl-3-phenylpropyl)piperidine.

MECHANISTIC ASPECTS OF FLUORIDE ION-CATALYZED REDUCTION OF CARBONYL COMPOUNDS WITH HYDROSILANES

Fluoride ion catalyzed reduction of aldehydes and ketones with hydrosilane in HMPA is found to involve a hexavalent silicate (1-) as the active hydride species, and no evidence is obtained for interaction of the carbonyl oxygen with the silic

CHEMOSELEKTIVE MONO- UND DISILYLETHERBILDUNG AUS TERTIAEREN UND SEKUNDAEREN SILANEN

Tertiary and secondary silanes are O-selective.With alcohols the corresponding silyl ethers are formed.Cesium fluoride/imidazole)CsF/Im) is a better activating system than CsF alone.Primary OH groups are silylated remarkably faster under CsF/Im activation