107116-05-2

Upstream product

• 17938-20-4 dimethylphenyl(phenylmethyl)silane 
• 932-31-0 ortho-tolylmagnesium bromide 
• 768-33-2 phenyldimethylsilyl chloride 
• 95-52-3 2-Fluorotoluene 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 

Downstream Products

• 107116-12-1 1,3-Bis(2-benzoylphenyl)-1,1,3,3-tetramethyldisiloxan 
• 107116-09-6 2-(Dimethylphenylsilyl)benzoylchlorid 
• 107116-08-5 2-(Dimethylphenylsilyl)benzoesaeure 
• 107116-07-4 ortho-dimethylphenylsilylbenzaldehyde 
• 107116-06-3 <2-(Dibrommethyl)phenyl>dimethylphenylsilan 

Relevant academic research and scientific papers

In Situ Generation of Silyl Anion Species through Si?B Bond Activation for the Concerted Nucleophilic Aromatic Substitution of Fluoroarenes

In situ generated silyl anion species enable the concerted nucleophilic aromatic substitution of fluoroarenes. Model DFT calculations indicated that addition of a base to a silylborane would thermodynamically form a silyl borate complex and then kinetically release a silyl anion species through Si?B bond cleavage, and that the in situ generated silyl anion equivalent would further react with a fluoroarene through a concerted nucleophilic aromatic substitution pathway with an activation barrier of ca. 20 kcal/mol to afford the silylated product with a large energy gain. Experiments confirmed that the defluorosilylation reaction took place smoothly at room temperature simply upon mixing fluoroarenes with commercially available silylborane and NaOtBu. Radical scavenger and radical clock reaction experiments provide further evidence for the in situ generation of the silyl anion.

METHOD FOR PREPARING SILAHYDROCARBONS

The present disclosure is directed to a process for preparing silahydrocarbons of formula (I), the process comprising the step of reacting a compound of formula (II), with a compound of formula (III), as well as to silahydrocarbons prepared by such a process, and to compositions and articles of manufacture comprising such silahydrocarbons.

Palladium-Catalyzed Cross-Coupling of Monochlorosilanes and Grignard Reagents

Using a palladium catalyst supported by DrewPhos, the alkylation of monochlorosilanes with primary and secondary alkylmagnesium halides is now possible. Arylation with sterically demanding aromatic magnesium halides is also enabled. This transformation ov

Zinc-catalyzed nucleophilic substitution reaction of chlorosilanes with organomagnesium reagents

Zinc-catalyzed nucleophilic substitution reactions of chlo-rosilanes with organomagnesium reagents afford various tetraorganosilanes under mild reaction conditions. The reactions can be performed on large scale and allow efficient preparation of functionalized tetraorganosilanes.

Copper-catalyzed arylation of chlorosilanes with grignard reagents

Nucleophilic substitution reactions of chlorosilanes with aryl Grignard reagents take place efficiently in the presence of copper(I) iodide to afford tetraorganosilanes.

Silver-catalyzed transmetalation between chlorosilanes and aryl and alkenyl Grignard reagents for the synthesis of tetraorganosilanes

(Chemical Equation Presented) The silver savior: Nucleophilic substitution reactions of chlorosilanes with aryl Grignard reagents have been developed which take place under silver catalysis to afford tetraorganosilanes (see scheme). This transformation is likely to be promoted by diarylargentate reagents that are generated in situ.

The one- and two-photon photochemistry of benzylsilacyclobutanes, acyclic benzylsilanes, and 1,1,2-triphenylsilacyclobutane

The photochemistry of several ∝-silylbenzyl compounds has been investigated in hexane and in methanol solution. Direct photolysis of 1-benzyl-1-methylsilacyclobutane (1) in methanolic hexane solution produces 1-propyl-1methyl-2,3-benzosilacyclobutene (6) in quantitative yield, by a sequential two-photon process involving the photoactive isotoluene derivative 1-methylene-6-(1-methylsilacyclobutyl)-2,4-cyclohexadiene (13a), which has been identified on the basis of its 1H NMR and UV absorption spectra. In contrast, direct irradiation of 1-benzyl-1-phenylsilacyclobutane (2) under similar conditions results in the formation of a complex mixture of products consistent with the competing formation of 1-benzyl-1-phenylsilene and benzyl- and 1-phenylsilacyclobutyl radicals. The silene is a transient which has been detected directly by laser flash photolysis of 2 (λmax = 315 nm, τ ～ 4.5 μs). Free radical formation is shown to be due to secondary photolysis of a second primary product, 1-methylene-6-(1-phenylsilacyclobutyl)-2,4-cyclohexadiene (13b), which has also been detected and identified by static UV absorption (λmax = 335 nm) and 1H NMR spectroscopy. In a reaction with some analogy to the acid-catalyzed desilylation of allylsilanes, both 13a and 13b can be intercepted in neutral or acidic methanol solution to yield toluene and 1-methyl- or 1-phenyl-1-methoxysilacyclobutane, respectively. Direct photolysis of benzyldimethylphenylsilane (4) also leads to the formation of the corresponding isotoluene derivative, while benzyltrimethylsilane (3) exhibits negligible photoreactivity. The endocyclic benzylsilane 1,1,2-triphenylsilacyclobutane (5) is shown to undergo competing [2 + 2]-cycloreversion and [1,3]-silyl migration to yield a bicyclic isotoluene analogue, which reacts rapidly with methanol to yield the acyclic methoxysilane reported previously to be the main product of photolysis of this silacyclobutane in methanol solution. Relative quantum yields for isotoluene formation from photolysis of 1-4 and absolute rate constants for methanolysis of several of these compounds under neutral and acidic conditions have also been determined.