1432-38-8

Upstream product

• 1066-35-9 dimethylmonochlorosilane 
• 14774-77-7 p-methoxyphenyllithium 
• 696-62-8 para-iodoanisole 
• 623-12-1 4-chloromethoxybenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 2372-33-0 chlorodimethyl(4-methoxyphenyl)silane 

Downstream Products

• 622382-76-7 2-[(4-methoxyphenyl)dimethylsilylmethylene]hexanal 
• 850636-01-0 C₂₈H₃₄O₂Si₂ 
• 929120-65-0 (E)-4-(dimethyl(4-methoxyphenyl)silyl)but-3-en-2-ol 
• 150-76-5 4-methoxy-phenol 
• 2372-33-0 chlorodimethyl(4-methoxyphenyl)silane 
• 482636-09-9 ethyl 2-[dimethyl(4-methoxyphenyl)silyl]ethanoate 
• 57769-33-2 Dichloromethyl-(4-methoxy-phenyl)-dimethyl-silane 

Relevant academic research and scientific papers

Metal-free hydrogen evolution cross-coupling enabled by synergistic photoredox and polarity reversal catalysis

A synergistic combination of photoredox and polarity reversal catalysis enabled a hydrogen evolution cross-coupling of silanes with H2O, alcohols, phenols, and silanols, which afforded the corresponding silanols, monosilyl ethers, and disilyl ethers, respectively, in moderate to excellent yields. The dehydrogenative cross-coupling of Si-H and O-H proceeded smoothly with broad substrate scope and good functional group compatibility in the presence of only an organophotocatalyst 4-CzIPN and a thiol HAT catalyst, without the requirement of any metals, external oxidants and proton reductants, which is distinct from the previously reported photocatalytic hydrogen evolution cross-coupling reactions where a proton reduction cocatalyst such as a cobalt complex is generally required. Mechanistically, a silyl cation intermediate is generated to facilitate the cross-coupling reaction, which therefore represents an unprecedented approach for the generation of silyl cationviavisible-light photoredox catalysis.

Selective Electrochemical Hydrolysis of Hydrosilanes to Silanols via Anodically Generated Silyl Cations

The first electrochemical hydrolysis of hydrosilanes to silanols under mild and neutral reaction conditions is reported. The practical protocol employs commercially available and cheap NHPI as a hydrogen-atom transfer (HAT) mediator and operates at room temperature with high selectivity, leading to various valuable silanols in moderate to good yields. Notably, this electrochemical method exhibits a broad substrate scope and high functional-group compatibility, and it is applicable to late-stage functionalization of complex molecules. Preliminary mechanistic studies suggest that the reaction appears to proceed through a nucleophilic substitution reaction of an electrogenerated silyl cation with H2O.

Catalytic Enantioselective Dehydrogenative Si-O Coupling to Access Chiroptical Silicon-Stereogenic Siloxanes and Alkoxysilanes

A rhodium-catalyzed enantioselective construction of triorgano-substituted silicon-stereogenic siloxanes and alkoxysilanes is developed. This process undergoes a direct intermolecular dehydrogenative Si-O coupling between dihydrosilanes with silanols or alocohols, giving access to a variety of highly functionalized chiral siloxanes and alkoxysilanes in decent yields with excellent stereocontrol, that significantly expand the chemical space of the silicon-centered chiral molecules. Further utility of this process was illustrated by the construction of CPL-active (circularly polarized luminescence) silicon-stereogenic alkoxysilane small organic molecules. Optically pure bis-alkoxysilane containing two silicon-stereogenic centers and three pyrene groups displayed a remarkable glum value with a high fluorescence quantum efficiency (glum = 0.011, φF = 0.55), which could have great potential application prospects in chiral organic optoelectronic materials.

Intermolecular Dehydrogenative C?H/Si?H Cross-Coupling for the Synthesis of Arylbenzyl Bis(silanes)

An iridium-catalyzed intermolecular dehydrogenative C?H/Si?H cross-coupling reaction for the synthesis of arylbenzyl bis(silanes) is developed. This hydrosilyl group steered intermolecular C?H silylation process features high chemo- and regioselectivity,

Silicon-center chiral silicon-oxygen compound and preparation method thereof

The invention belongs to the field of chiral silicon synthesis, and discloses a silicon-center chiral silicon-oxygen compound. The compound has a structure represented by general formula I shown in the specification. In the formula I, X is Si(R)n or a formula also shown in the specification, R is selected from alkyl, cycloalkyl and aryl, R is selected from alkyl, substituted phenyl and aryl, R is selected from alkyl, phenyl and substituted phenyl, n is 3, the three R are the same or different, R is selected from hydrogen and (C1-C4) alkyl, m is selected from 0, 1, 2 and 3, and Y is selected from substituted phenyl, substituted pyrenyl, aryl, heteroaryl and cycloalkyl. The invention also discloses a preparation method of the compound. Various highly functionalized chiral siloxanes and silyl ethers are obtained with good chemical, regional and stereo control and high yield, the variety of silicon center chiral compounds is expanded, and the method has the advantages of high enantioselectivity, wide substrate application range, mild reaction conditions, atom economy and the like. In addition, the compound provided by the invention has a huge application prospect in chiral organic photoelectric materials.

Selective Manganese-Catalyzed Oxidation of Hydrosilanes to Silanols under Neutral Reaction Conditions

The first manganese-catalyzed oxidation of organosilanes to silanols with H2O2 under neutral reaction conditions has been accomplished. A variety of organosilanes with alkyl, aryl, alknyl, and heterocyclic substituents were tolerated, as well as sterically hindered organosilanes. The oxidation appears to proceed by a concerted process involving a manganese hydroperoxide species. Featuring mild reaction conditions, fast oxidation, and no waste byproducts, the protocol allows a low-cost, eco-benign synthesis of both silanols and silanediols.

Au Nanoparticle-Catalyzed Insertion of Carbenes from α-Diazocarbonyl Compounds into Hydrosilanes

Supported Au nanoparticles on TiO2 catalyze the insertion of carbenes from α-diazocabonyl compounds into hydrosilanes. It is proposed that the transformation involves two modes of catalytic activation: formation of nucleophilic Au carbenes on the surface of nanoparticle via expulsion of N2 and activation of the Si-H bond of hydrosilane on Au nanoparticle, followed by coupling of the chemisorbed species. No external ligands or additives are required, while the process is purely heterogeneous, thus allowing the recycling and reuse of the catalyst.

Rhodium-catalyzed carbonylative synthesis of silyl-substituted indenones

A novel and efficient rhodium-catalyzed procedure for the preparation of silyl-substituted indenones has been developed. Using silanes and internal alkynes as the substrates, in the presence of CO, good to excellent yields of the desired indenones were isolated. A wide range of functional groups, encompassing esters, amines, nitriles and halides, is compatible in this system.

Heme Protein Catalysts for Carbon-Silicon Bond Formation In Vitro and In Vivo

The present invention provides compositions and methods for catalyzing the formation of carbon-silicon bonds using heme proteins. In certain aspects, the present invention provides heme proteins, including variants and fragments thereof, that are capable of carrying out in vitro and in vivo carbene insertion reactions for the formation of carbon-silicon bonds. In other aspects, the present invention provides methods for producing an organosilicon product, the method comprising providing a silicon-containing reagent, a carbene precursor, and a heme protein; and combining the components under conditions sufficient to produce an organosilicon product. Host cells expressing the heme proteins are also provided by the present invention.

Effects of substituents on silicon atoms upon absorption and fluorescence properties of 1,3,6,8-tetrakis(silylethynyl)pyrenes

Synthesis, UV–vis absorption, and fluorescence spectroscopic properties of 1,3,6,8-tetrakis(silylethynyl)pyrenes 2–10 were studied. Absorption maxima of CH2Cl2 solutions of these compounds appeared at 437–445 nm, and molar absorption coefficients (ε) of most of these compounds exceeded 105 L mol?1 cm?1. Fluorescence emissions measured in dilute CH2Cl2 solutions are observed in visible region, and their intensities remarkably increased compared with that of pyrene. Fluorescence spectra obtained from concentrated CH2Cl2 solutions exhibited broad excimer emissions when steric bulk of substituents on silicon atoms is sufficiently low. Molecular orbital calculations indicated that HOMO-LUMO energy gap decreased with increasing the number of phenyl groups on silicon atoms, and that the silyl groups act as electron-donating groups to tetraethynylpyrene core. Resonances in 29Si NMR spectra shifts to upfield with increasing the number of phenyl groups on silicon atoms due to the shielding effect of phenyl groups.