18858-69-0

Usage

Uses

Used in Organic Synthesis:
(Benzyloxy)triphenylsilane is used as a versatile reagent for constructing carbon-carbon and carbon-heteroatom bonds in the synthesis of pharmaceuticals, agrochemicals, and materials. Its ability to undergo cross-coupling reactions, hydrosilylation, and radical reactions makes it a valuable tool in this application.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (benzyloxy)triphenylsilane is utilized as a key intermediate in the synthesis of various drugs, contributing to the development of novel therapeutic agents.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, (benzyloxy)triphenylsilane serves as a crucial component in the creation of new pesticides and other agricultural chemicals, enhancing crop protection and yield.
Used in Material Science:
(Benzyloxy)triphenylsilane is also employed in material science for the development of advanced materials with specific properties, such as improved strength, durability, or chemical resistance, thanks to its role in forming carbon-heteroatom bonds.

Upstream product

• 1256450-18-6 N-cyclohexyl(triphenylsilyl)methaneamide 
• 100-51-6 benzyl alcohol 
• 116-14-3 polytetrafluoroethylene 
• 100-52-7 benzaldehyde 
• 789-25-3 HSiPh₃ 
• 1171-49-9 benzoyl-triphenyl-silane 
• 76-86-8 Triphenylsilyl chloride 
• 791-30-0 triphenylsilyl-lithium 
• 18858-71-4 phenyl-triphenylsilanyl-methanol 

Downstream Products

• 108-88-3 toluene 
• 791-31-1 triphenylhydroxysilane 
• 1861-00-3 deuteriomethyl-benzene 
• 18536-59-9 C₁₈H₁₅⁽²⁾HOSi 
• 100-51-6 benzyl alcohol 
• 1361991-02-7 1,1-dimethyl-3,3,3-triphenyl-3,3-1-vinyldisiloxane 
• 799-53-1 1,1,1-trimethyl-3,3,3-triphenyl-disiloxane 
• 18858-71-4 phenyl-triphenylsilanyl-methanol 

Relevant academic research and scientific papers

Synthesis and catalytic activity of N-heterocyclic silylene (NHSi) iron (II) hydride for hydrosilylation of aldehydes and ketones

A novel silylene supported iron hydride [Si, C]FeH (PMe3)3 (1) was synthesized by C (sp3)-H bond activation with zero-valent iron complex Fe (PMe3)4. Complex 1 was fully characterized by spectroscopic methods and single crystal X-ray diffraction analysis. To the best of our knowledge, 1 is the first example of silylene-based hydrido chelate iron complex produced through activation of the C (sp3)?H bond. It was found that complex 1 exhibited excellent catalytic activity for hydrosilylation of aldehydes and ketones. The catalytic system showed good tolerance and catalytic activity for the substrates with different functional groups on the benzene ring. It is worth mentioning that, the experimental results showed that both ketones and aldehydes could be reduced in good to excellent yields under the same catalytic conditions. Based on the experiments and literature reports, a possible catalytic mechanism was proposed.

Heavier Alkaline-Earth Catalyzed Dehydrocoupling of Silanes and Alcohols for the Synthesis of Metallo-Polysilylethers

The dehydrocoupling of silanes and alcohols mediated by heavier alkaline-earth catalysts, [Ae{N(SiMe3)2}2?(THF)2] (I–III) and [Ae{CH(SiMe3)2}2?(THF)2], (IV–VI) (Ae=Ca, Sr, Ba) is described. Primary, secondary, and tertiary alcohols were coupled to phenylsilane or diphenylsilane, whereas tertiary silanes are less tolerant towards bulky substrates. Some control over reaction selectivity towards mono-, di-, or tri-substituted silylether products was achieved through alteration of reaction stoichiometry, conditions, and catalyst. The ferrocenyl silylether, FeCp(C5H4SiPh(OBn)2) (2), was prepared and fully characterized from the ferrocenylsilane, FeCp(C5H4SiPhH2) (1), and benzyl alcohol using barium catalysis. Stoichiometric experiments suggested a reaction manifold involving the formation of Ae–alkoxide and hydride species, and a series of dimeric Ae–alkoxides [(Ph3CO)Ae(μ2-OCPh3)Ae(THF)] (3 a–c, Ae=Ca, Sr, Ba) were isolated and fully characterized. Mechanistic experiments suggested a complex reaction mechanism involving dimeric or polynuclear active species, whose kinetics are highly dependent on variables such as the identity and concentration of the precatalyst, silane, and alcohol. Turnover frequencies increase on descending Group 2 of the periodic table, with the barium precatalyst III displaying an apparent first-order dependence in both silane and alcohol, and an optimum catalyst loading of 3 mol % Ba, above which activity decreases. With precatalyst III in THF, ferrocene-containing poly- and oligosilylethers with ferrocene pendent to- (P1–P4) or as a constituent (P5, P6) of the main polymer chain were prepared from 1 or Fe(C5H4SiPhH2)2 (4) with diols 1,4-(HOCH2)2-(C6H4) and 1,4-(CH(CH3)OH)2-(C6H4), respectively. The resultant materials were characterized by NMR spectroscopy, gel permeation chromatography (GPC) and DOSY NMR spectroscopy, with estimated molecular weights in excess of 20,000 Da for P1 and P4. The iron centers display reversible redox behavior and thermal analysis showed P1 and P5 to be promising precursors to magnetic ceramic materials.

Nickel-Catalyzed Three-Component Coupling Reaction of Tetrafluoroethylene and Aldehydes with Silanes via Oxa-Nickelacycles

The nickel-catalyzed synthesis of a variety of fluorine-containing silyl ethers from tetrafluoroethylene (TFE) and aldehydes with silanes in a selective manner is disclosed. Stoichiometric reactions revealed that the oxa-nickelacycle, which is generated u

Mild synthesis of silyl ethers: Via potassium carbonate catalyzed reactions between alcohols and hydrosilanes

A method has been developed for the silanolysis of alcohols using an abundant and non-corrosive base K2CO3 as a catalyst. Reactions between a variety of alcohols and hydrosilanes generate silyl ethers under mild conditions. The use of hydrosilanes leads to the formation of H2 as the only byproduct thus avoiding the formation of stoichiometric strong acids. The mild conditions lead to a wide scope of possible alcohol substrates and good functional group tolerance. Selective alcohol silanolysis is also observed in the presence of reactive C-H bonds, lending this method for extensive use in protection group chemistry.

Cationic rhenium(iii) complexes: synthesis, characterization, and reactivity for hydrosilylation of aldehydes

A series of novel cationic Re(iii) complexes [(DAAm)Re(CO)(NCCH3)2][X] [DAAm = N,N-bis(2-arylaminoethyl)methylamine; aryl = C6F5 (a), Mes (b)] [X = OTf (2), BArF4 [BArF4 = tetrakis[3,5-(trifluoromethyl)phenyl]borate] (3), BF4 (4), PF6 (5)], and their analogue [(DAmA)Re(CO)(Cl)2] [DAmA = N,N-bis(2-arylamineethyl)methylamino; aryl = C6F5] (6) were synthesized. The catalytic efficiency for the hydrosilylation reaction of aldehydes using 4a (0.03 mol%) has been demonstrated to be significantly more active than rhenium catalysts previously reported in the literature. The data suggest that electron-withdrawing substituents at the diamido amine ligand increase the catalytic efficiency of the complexes. Excellent yields were achieved at ambient temperature under neat conditions using dimethylphenylsilane. The reaction affords TONs of up to 9200 and a TOF of up to 126 h-1. Kinetic and mechanistic studies were performed, and the data suggest that the reaction is via a non-hydride ionic hydrosilylation mechanism.

Exploring Multistep Continuous-Flow Hydrosilylation Reactions Catalyzed by Tris(pentafluorophenyl)borane

Exploring the combination of continuous-flow processes with the boron Lewis acid catalyzed hydrosilylation of aldehydes and ketones has delivered a robust and generally applicable reaction protocol. Notably this approach permits ready access to high temperatures and pressures and thus allows improved reactivity of substrates that were previously recalcitrant under the traditional approach. Efforts to quench the output from the flow reactor with water showed surprising tolerance leading to the application of continuous-flow systems in multistep imine formation/hydrosilylation processes to generate the corresponding secondary amines from their aldehyde and aniline precursors. (Figure presented.).

Silanol Compound, Composition, and Method for Producing Silanol Compound

The purpose of the present invention is to provide silanol compounds that can be used as raw materials of siloxane compounds and the like, and a composition of the silanol compounds, as well as to provide a production method that makes it possible to produce silanol compounds at excellent yield. A composition comprising 5 mass % to 100 mass % of a silanol compound represented by Formulas (A) to (C) can be prepared by devising to produce silanol compounds under water-free conditions, to produce silanol compounds in a solvent having the effect of suppressing the condensation of silanol compounds, and to perform other such processes, the composition being able to be used as a raw material or the like of siloxane compounds because the silanol compounds can be stably present in the resulting composition.

Dehydrogenative Coupling of Hydrosilanes and Alcohols by Alkali Metal Catalysts for Facile Synthesis of Silyl Ethers

Cross-dehydrogenative coupling (CDC) of hydrosilanes with hydroxyl groups, using alkali metal hexamethyldisilazide as a single-component catalyst for the formation of Si-O bonds under mild condition, is reported. The potassium salt [KN(SiMe3)2] is highly efficient and chemoselective for a wide range of functionalized alcohols (99% conversion) under solvent-free conditions. The CDC reaction of alcohols with silanes exhibits first-order kinetics with respect to both catalyst and substrate concentrations. The most plausible mechanism for this reaction suggests that the initial step most likely involves the formation of an alkoxide followed by the formation of metal hydride as active species.

N-Methyl-Benzothiazolium Salts as Carbon Lewis Acids for Si?H σ-Bond Activation and Catalytic (De)hydrosilylation

N?Me-Benzothiazolium salts are introduced as a new family of Lewis acids able to activate Si?H σ bonds. These carbon-centred Lewis acids were demonstrated to have comparable Lewis acidity towards hydride as found for the triarylboranes widely used in Si?H σ-bond activation. However, they display low Lewis acidity towards hard Lewis bases such as Et3PO and H2O in contrast to triarylboranes. The N?Me-benzothiazolium salts are effective catalysts for a range of hydrosilylation and dehydrosilylation reactions. Judicious selection of the C2 aryl substituent in these cations enables tuning of the steric and electronic environment around the electrophilic centre to generate more active catalysts. Finally, related benzoxazolium and benzimidazolium salts were found also to be active for Si?H bond activation and as catalysts for the hydrosilylation of imines.

Method for producing polyimidesiloxane

PROBLEM TO BE SOLVED: To provide a method for synthesizing siloxanes at will in good yield while maintaining high structural controllability, which can be applied to substrates having various substituents.SOLUTION: The method comprises reacting benzyloxysilanes and silicon halides in the absence of hydrogen using a catalyst comprising a transition metal or a compound thereof, preferably a metal of group 9 or group 10 of the periodic table or a compound thereof. Thereby, corresponding siloxanes can be produced safely and simply in high yield under a mild reaction condition accompanied by elimination of a benzyl halide. Especially, by using an active carbon-supported catalyst as a heterogeneous catalyst, the target siloxanes can be separated easily.