21130-91-6

Usage

Uses

A silicon-based nucleophile shown to be reactive in Pd-catalyzed cross-coupling reactions.

InChI:InChI=1/C13H22O4Si/c1-5-15-18(16-6-2,17-7-3)13-10-8-12(14-4)9-11-13/h8-11H,5-7H2,1-4H3

Upstream product

• 998-30-1 Triethoxysilane 
• 696-62-8 para-iodoanisole 
• 78-10-4 tetraethoxy orthosilicate 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 66107-29-7 4-methoxyphenyl triflate 
• 123155-78-2 4-methoxybenzenediazonium 4-methylbenzenesulfonate 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 40141-09-1 3-(4-methoxyphenyl)cyclohexene 
• 13021-18-6 1-(4'-methoxy-biphenyl-4-yl)-ethanone 
• 173464-57-8 (E)-3-(4-methoxyphenyl)acrylic acid butyl ester 
• 92804-32-5 3-(4-methoxyphenyl)-3-phenylpropanal 
• 62557-94-2 (R,S)-3-p-methoxyphenyl-1-phenylbutan-1-one 
• 107752-76-1 2-methoxy-5-(4'-methoxyphenyl)cyclohepta-2,4,6-trien-1-one 
• 613-37-6 4-methoxylbiphenyl 
• 1186241-71-3 N-(3-(4-methoxyphenyl)-2H-chromen-4-yl)acetamide 
• 20442-73-3 (1E)-3-(4-methoxyphenyl)-1-phenylpropene 
• 72046-76-5 4,4'-((4-methoxy-1,3-phenylene)bis(methylene))bis(methoxybenzene) 
• 834-14-0 p-benzylanizole 
• 80448-01-7 p-methoxyphenyl phenyl selenide 
• 459-60-9 1-fluoro-4-methoxybenzene 

Relevant academic research and scientific papers

Rhodium(III)-Catalyzed Direct C-H Arylation of Various Acyclic Enamides with Arylsilanes

The stereoselective β-C(sp2)-H arylation of various acyclic enamides with arylsilanes via Rh(III)-catalyzed cross-coupling reaction was illustrated. The methodology was characterized by extraordinary efficacy and stereoselectivity, a wide scope of substrates, good functional group tolerance, and the adoption of environmentally friendly arylsilanes. The utility of this present method was evidenced by the gram-scale synthesis and further elaboration of the product. In addition, Rh(III)-catalyzed C-H activation is considered to be the critical step in the reaction mechanism.

High refractive index organic silicon resin and its preparation method and application

The invention relates to organic silicon resin with high refractive index, a preparation method and an application thereof. Particularly, in the manufacturing process of the organic silicon resin, the organic silicon resin with high refractive index can be obtained by adding monomers shown in a formula I into a reaction system; in the formula, R1 and R2 are defined as the description in the specification. The organic silicon resin prepared by the invention is high in refractive index and can be used as an organic silicon adhesive in the field of LED (Light Emitting Diode) package.

One-pot synthesis and structural characterization of poly(alkoxysilane)s catalyzed by silver-gold complexes

Combinative one-pot Si-Si/Si-O dehydrocoupling of hydrosilanes with alcohols (1:1.5 mole ratio), mediated by a mixture of AgNO3-AuCl 3 (100/1 mole ratio) rapidly produced poly(alkoxysilane)s in reasonably high yield. The addition of small amount of gold complex to the reaction mixture effectively accelerated the coupling reaction compared to the reaction rate with AgNO3 alone. The hydrosilanes include p-X-C 6H4SiH3 (X = H, CH3, OCH 3, F), PhCH2SiH3, and (PhSiH2) 2. The alcohols include MeOH, EtOH, iPrOH, PhOH, and CF 3(CF2)2CH2OH. The weight average molecular weight and polydispersity of the poly(alkoxysilane)s were in the range of 1,600～8,000 Dalton and 1.4～3.5, respectively. The dehydrocoupling reactions of phenylsilane with ethanol (1:3 mole ratio) in the presence of the Ag-Au complexes gave only triethoxyphenylsilane. Copyright

Meerwein's reagent mediated, significantly enhanced nucleophilic fluorination on alkoxysilanes

We developed a new facile method to fluorosilanes from alkoxysilanes using Meerwein's reagent. Our protocol afforded fluorosilanes in excellent yields in various organic solvents including acetonitrile under mild reaction conditions at room temperature. We also proposed a reaction mechanism with the probable silyloxonium intermediates. Georg Thieme Verlag Stuttgart · New York.

Rhodium(I)-catalyzed synthesis of aryltriethoxysilanes from arenediazonium tosylate salts with triethoxysilane

An efficient method for the preparation of aryltriethoxy-silanes from arenediazonium tosylate salts has been developed, which expands the substrates of rhodium-catalyzed silylation from iodides, bromides, and triflates to diazonium salts. A new method for hydrodediazoniation has also been explored.

Synthesis of aryltriethoxysilanes via rhodium(I)-catalyzed cross-coupling of aryl electrophiles with triethoxysilane

The general and efficient silylation of aryl halides has been developed utilizing triethoxysilane and a rhodium catalyst. The substrate scope is broad and includes ortho-, meta-, and para-substituted electron-rich and -deficient aryl iodides. In addition, the silylation of aryl bromides and fluoroalkanesulfonates proceeded in the presence of tetra-n-butylammonium iodide.

A facile and efficient synthesis of aryltriethoxysilanes via sonochemical Barbier-type reaction

A series of aryltriethoxysilanes was synthesized from the reaction mixture of aryl bromide, Mg powder, 1,2-dibromoethane and tetraethyl orthosilicate in THF under ultrasound. This sonochemical Barbier-type reaction provides a simple and efficient method for preparation of aryltriethoxysilanes. The Hiyama cross-coupling reaction of phenyltriethoxysilane with bromobenzene was investigated under different palladium catalysts and Pd(PhCN)2Cl2 was found to be the best choice.

Improved synthesis of aryltrialkoxysilanes via treatment of aryl Grignard or lithium reagents with tetraalkyl orthosilicates

General reaction conditions for the synthesis of aryl(trialkoxy)silanes from aryl Grignard and lithium reagents and tetraalkyl orthosilicates (Si(OR)4) have been developed. Ortho-, meta-, and para-substituted bromoarenes underwent efficient metalation and silylation at low temperature to provide aryl siloxanes. Mixed results were obtained with heteroaromatic substrates: 3-bromothiophene, 3-bromo-4-methoxypyridine, 5-bromoindole, and N-methyl-5-bromoindole underwent silylation in good yield, whereas a low yield of siloxane was obtained from 2-bromofuran, and 2-bromopyridine failed to give silylated product. The synthesis of siloxanes via organolithium and magnesium reagents was limited by the formation of di- and triarylated silanes (Ar 2Si(OR)2 and Ar3SiOR, respectively) and dehalogenated (Ar-H) byproducts. Silylation at low temperature gave predominantly monoaryl siloxanes, without requiring a large excess of the electrophile. Optimal reaction conditions for the synthesis of siloxanes from aryl Grignard reagents entailed addition of arylmagnesium reagents to 3 equiv of tetraethyl- or tetramethyl orthosilicate at -30 °C in THF. Aryllithium species were silylated using 1.5 equiv of tetraethyl- or tetramethyl orthosilicate at -78 °C in ether.

One-pot synthesis of poly(alkoxysilane)s by Si-Si/Si-O dehydrocoupling of silanes with alcohols using Group IV and VIII metallocene complexes

Si-Si/Si-O dehydrocoupling reactions of silanes with alcohols (1:1.5 mole ratio), catalyzed by Cp2MCl2/Red-Al (M=Ti, Zr) and Cp2M′ (M′=Co, Ni), produced poly(alkoxysilane)s in one-pot in high yield. The silanes included p-X-C6H4SiH3 (X=H, CH3, OCH3, F), PhCH2SiH3, and (PhSiH2)2. The alcohols were MeOH, EtOH, iPrOH, PhOH, and CF3(CF2) 2CH2OH. The weight average molecular weight of the poly(alkoxysilane)s ranged from 600 to 8000. The dehydrocoupling reactions of phenylsilane with ethanol (1:1.5 mole ratio) using Cp2HfCl2/Red-Al and phenylsilane with ethanol (1:3 mole ratio) using Cp2TiCl2/Red-Al gave only triethoxyphenylsilane as product.

Rhodium(I)-Catalyzed Silylation of Aryl Halides with Triethoxysilane: Practical Synthetic Route to Aryltriethoxysilanes

(Equation Presented) The specific silylation of aryl iodides and bromides with triethoxysilane (EtO)3SiH in the presence of NEt3 and a catalytic amount of [Rh-(cod)(MeCN)2]BF4 provides the corresponding aryltriethoxysilanes in high yield.