2987-77-1

Usage

Uses

Used in Organic Synthesis:
Triethyl(phenyl)silane is used as a reducing agent for facilitating reduction reactions in organic synthesis. It donates a hydride ion to selectively reduce functional groups such as ketones, aldehydes, imines, and double bonds, making it a valuable tool in the preparation of complex organic molecules.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, triethyl(phenyl)silane is utilized as a reagent in the synthesis of various drugs. Its mild reaction conditions and high efficiency contribute to the production of pharmaceuticals with fewer side reactions and improved yields.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical sector, triethyl(phenyl)silane is employed for the synthesis of agrochemicals. Its selective reduction capabilities are advantageous in creating specific agrochemical compounds with desired properties.
Used in Fine Chemicals Production:
Triethyl(phenyl)silane is also used in the production of fine chemicals, where its selective reduction properties are beneficial for creating high-purity specialty chemicals required in various applications.

Upstream product

• 994-30-9 triethylsilyl chloride 
• 71-43-2 benzene 
• 24669-77-0 triethylsilane radical 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 591-51-5 phenyllithium 
• 197797-33-4 triethylsilyl tris(trimethylsilyl)silanecarboxylate 
• 100-47-0 benzonitrile 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 
• 92465-73-1 triethylsilylcalcium chloride 
• 462-06-6 fluorobenzene 
• 98-13-5 Phenyltrichlorosilane 
• 557-20-0 diethylzinc 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 451-40-1 phenyl benzyl ketone 
• 631-36-7 triethylsilane 
• 1633-09-6 hexaethyldisilane 
• 994-49-0 hexaethyl disiloxane 
• 17964-10-2 diethyl-diphenyl-silane 
• 14315-12-9 3-phenyl-1-benzothiophene 
• 92-52-4 biphenyl 
• 18751-07-0 diphenyl-(4-triethylsilanyl-phenyl)-arsine 
• 1567-38-0 1,2-diphenyl-ethanone semicarbazone 
• 71-43-2 benzene 
• 18037-03-1 (4-chlorophenyl)triethylsilane 
• 495-40-9 propiophenone 
• 119-61-9 benzophenone 
• 18106-49-5 (4-aminophenyl)triethylsilane 

Relevant academic research and scientific papers

Iridium-catalyzed intermolecular dehydrogenative silylation of polycyclic aromatic compounds without directing groups

This study describes the iridium-catalyzed intermolecular dehydrogenative silylation of C(sp2)-H bonds of polycyclic aromatic compounds without directing groups. The reaction produced various arylsilanes through both Si-H and C-H bond activation, with hydrogen as the sole byproduct. Reactivity was affected by the electronic nature of the aromatic compounds, and silylation of elec-tron-deficient and polycyclic aromatic compounds proceeded efficiently. Site-selectivity was controlled predominantly by steric factors. Therefore, the current functionalization proceeded with opposite chemo- and site-selectivity compared to that observed for general electrophilic functionalization of aromatic compounds.

INSERTION REACTIONS OF CALCIUM ATOM INTO Si-Cl AND Ge-Cl BONDS

Calcium atom is inserted into Si-Cl and Ge-Cl bonds of organosilylchlorides and organogermylchlorides to give the corresponding organosilylcalcium chlorides and organogermylcalcium chlorides, respectively.

Absolute Rate Constants for the Addition of Trimethylsilyl Radicals to Various Unsuturated Compounds

The absolute rate constants for the reaction of Et3Si. radicals with a large number of unsaturated compounds have been measured by laser flash photolysis techniques.The reactivities of C=C double bonds have a wide range, e.g., the rate constants at ca. 300 K are 1.1x109, 2.2x108, 1.0x107, 3.7x106, and 9.4x105 M-1 s-1 for acrylonitrile, styrene, tetrachloroethylene, 1-hexene, and cyclohexene, respectively.The range of reactivities for addition to aromatic and heteroaromatic compounds is rather small, the rate constants at ca. 300 K varying from 4.6x105 M-1 s-1 for benzene to 5.0x106 M-1 s-1 for thiophene and α-methylnaphthalene.Acetylenes are slightly less reactive than structurally analogous 1-olefins.For the other types of multiple bonds examined, reactivities decreased in the order isocyanide > nitrone > nitro > isocyanate > nitrile.Arrhenius parameters were determined for a few olefins including ethylene, for which an EPR spectroscopic competition procedure was required.For styrene, log (A/(M-1 s-1)) = 9.35 +/- 0.23 and Ea = 1.37 +/- 0.29 kcal/mol; for ethylene, log (A/(M-1 s-1))= 8.40 +/- 0.60 and Ea = 1.40 +/- 0.80 kcal/mol.

Continuous-flow Si-H functionalizations of hydrosilanesviasequential organolithium reactions catalyzed by potassiumtert-butoxide

We herein report an atom-economic flow approach to the selective and sequential mono-, di-, and tri-functionalizations of unactivated hydrosilanesviaserial organolithium reactions catalyzed by earth-abundant metal compounds. Based on the screening of various additives, we found that catalytic potassiumtert-butoxide (t-BuOK) facilitates the rapid reaction of organolithiums with hydrosilanes. Using a flow microreactor system, various organolithiums bearing functional groups were efficiently generatedin situunder mild conditions and consecutively reacted with hydrosilanes in the presence oft-BuOK within 1 min. We also successfully conducted the di-funtionalizations of dihydrosilane by sequential organolithium reactions, extending to a gram-scale-synthesis. Finally, the combinatorial functionalizations of trihydrosilane were achieved to give every conceivable combination of tetrasubstituted organosilane libraries based on a precise reaction control using an integrated one-flow system.

Generation of Aryllithium Reagents from N -Arylpyrroles Using Lithium

Treatment of 1-aryl-2,5-diphenylpyrroles with lithium powder in tetrahydrofuran at 0 °C results in the generation of the corresponding aryllithium reagents through reductive C-N bond cleavage.

?-Silicon-effect-promoted intermolecular site-selective C(sp3)-H amination with dirhodium nitrenes

A dirhodium-catalyzed, ?-selective C-H amination of organosilicon compounds has been developed. Primary C(sp3)-H bonds of silylethyl groups and secondary C(sp3)-H bonds of silacycloalkanes can be selectively converted to C-N bonds at the ?-position of the silicon atoms. The experimental data and theoretical calculations indicate that the strong s-donor ability of the carbon-silicon bonds is responsible for the ?-selectivity. Kinetic isotope effects clearly demonstrate that the C-H bond cleavage step is not turnover-limiting, but selectivity-determining.

Silylation of Aryl Chlorides by Bimetallic Catalysis of Palladium and Gold on Alloy Nanoparticles

Supported palladium-gold alloy-catalyzed cross-coupling of aryl chlorides and hydrosilanes enabled the selective formation of aryl-silicon bonds. Whereas a monometallic palladium catalyst predominantly promoted the hydrodechlorination of aryl chlorides and gold nanoparticles showed no catalytic activity, gold-rich palladium-gold alloy nanoparticles efficiently catalyzed the title reaction to give arylsilanes with high selectivity. A wide array of aryl chlorides and hydrosilanes participated in the heterogeneously-catalyzed reaction to furnish the corresponding arylsilanes in 34–80% yields. A detailed mechanistic investigation revealed that palladium and gold atoms on the surface of alloy nanoparticles independently functioned as active sites for the formation of aryl nucleophiles and silyl electrophiles, respectively, which indicates that palladium and gold atoms on alloy nanoparticles work together to enable the selective formation of aryl-silicon bonds. (Figure presented.).

A Mild and Direct Site-Selective sp2 C-H Silylation of (Poly)Azines

A base-mediated protocol that allows for the site-selective sp2 C-H silylation of azines is described. This method is distinguished by its mild conditions, simplicity and excellent site-selective modulation for a diverse set of azines, even in the context of late-stage functionalization, while exhibiting orthogonal reactivity with classical silylation reactions.

Neutral-Eosin-Y-Photocatalyzed Silane Chlorination Using Dichloromethane

Chlorosilanes are versatile reagents in organic synthesis and material science. A mild pathway is now reported for the quantitative conversion of hydrosilanes to silyl chlorides under visible-light irradiation using neutral eosin Y as a hydrogen-atom-transfer photocatalyst and dichloromethane as a chlorinating agent. Stepwise chlorination of di- and trihydrosilanes was achieved in a highly selective fashion assisted by continuous-flow micro-tubing reactors. The ability to access silyl radicals using photocatalytic Si?H activation promoted by eosin Y offers new perspectives for the synthesis of valuable silicon reagents in a convenient and green manner.

Base-Mediated Defluorosilylation of C(sp2)?F and C(sp3)?F Bonds

The ability to selectively forge C–heteroatom bonds by C?F scission is typically accomplished by metal catalysts, specialized ligands and/or harsh reaction conditions. Described herein is a base-mediated defluorosilylation of unactivated C(sp2)?F and C(sp3)?F bonds that obviates the need for metal catalysts. This protocol is characterized by its simplicity, mild reaction conditions, and wide scope, even within the context of late-stage functionalization, constituting a complementary approach to existing C?Si bond-forming protocols.