- A convenient method for the protodesilylation of aryltrimethylsilanes
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A mild and highly effective procedure for the removal of aromatic trimethylsilyl groups involving treatment of ArSiMe3 with Me3SiCl, KI and H2O in acetonitrile, is reported.
- Radner, Finn,Wistrand, Lars-G.
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- Palladium-catalyzed silylation of aryl chlorides with hexamethyldisilane
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A method for the palladium-catalyzed silylation of aryl chlorides has been developed. The method affords desired product in good yield, is tolerant of a variety of functional groups, and provides access to a wide variety of aryltrimethylsilanes from commercially available aryl chlorides. Additionally, a one-pot procedure that converts aryl chlorides into aryl iodides has been developed.
- McNeill, Eric,Barder, Timothy E.,Buchwald, Stephen L.
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Read Online
- Expanding the Chemical Space of Succinate Dehydrogenase Inhibitors via the Carbon-Silicon Switch Strategy
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The carbon-silicon switch strategy has become a key technique for structural optimization of drugs to widen the chemical space, increase drug activity against targeted proteins, and generate novel and patentable lead compounds. Flubeneteram, targeting succinate dehydrogenase (SDH), is a promising fungicide candidate recently developed in China. We describe the synthesis of novel SDH inhibitors with enhanced fungicidal activity to enlarge the chemical space of flubeneteram by employing the C-Si switch strategy. Several of the thus formed flubeneteram-silyl derivatives exhibited improved fungicidal activity against porcine SDH compared with the lead compound flubeneteram and the positive controls. Disease control experiments conducted in a greenhouse showed that trimethyl-silyl-substituted compound W2 showed comparable and even higher fungicidal activities compared to benzovindiflupyr and flubeneteram, respectively, even with a low concentration of 0.19 mg/L for soybean rust control. Furthermore, compound W2 encouragingly performed slightly better control than azoxystrobin and was less active than benzovindiflupyr at the concentration of 100 mg/L against soybean rust in field trials. The computational results showed that the silyl-substituted phenyl moiety in W2 could form strong van der Waals (VDW) interactions with SDH. Our results indicate that the C-Si switch strategy is an effective method for the development of novel SDH inhibitors.
- Wei, Ge,Huang, Ming-Wei,Wang, Wen-Jie,Wu, Yuan,Mei, Shu-Fen,Zhou, Li-Ming,Mei, Long-Can,Zhu, Xiao-Lei,Yang, Guang-Fu
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p. 3965 - 3971
(2021/05/04)
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- Generation of Aryllithium Reagents from N -Arylpyrroles Using Lithium
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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.
- Ozaki, Tomoya,Kaga, Atsushi,Saito, Hayate,Yorimitsu, Hideki
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p. 3019 - 3028
(2021/06/02)
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- Method for preparing alcohol and phenol through aerobic hydroxylation reaction of boric acid derivative in absence of photocatalyst
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The invention discloses a method for preparing alcohol and phenol through aerobic hydroxylation reaction of a boric acid derivative in the absence of a photocatalyst, wherein the boric acid derivativeis aryl boronic acid or alkyl boronic acid, and the corresponding target compounds are respectively a phenol-based compound and an alcohol-based compound. According to the method, by using a boric acid derivative as a reaction substrate, an additive is added under a solvent condition, and a hydroxylation reaction is performed under aerobic and illumination conditions to obtain a corresponding target compound. According to the invention, the new strategy is provided for the synthesis of phenols through aerobic hydroxylation of aryl boronic acid without a photocatalyst; the catalyst-free aerobic hydroxylation method for photocatalysis of aryl boronic acid or alkyl boronic acid by using triethylamine as an additive is firstly disclosed; and the new method has advantages of photocatalyst-freecondition, wide substrate range and good functional group compatibility.
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Paragraph 0025-0028; 0030-0032
(2020/01/25)
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- Photoinduced hydroxylation of arylboronic acids with molecular oxygen under photocatalyst-free conditions
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Photoinduced hydroxylation of boronic acids with molecular oxygen under photocatalyst-free conditions is reported, providing a green entry to a variety of phenols and aliphatic alcohols in a highly concise fashion. This new protocol features photocatalyst-free conditions, wide substrate scope and excellent functional group compatibility.
- Xu, Yu-Ting,Li, Chen-Yuan,Huang, Xiao-Bo,Gao, Wen-Xia,Zhou, Yun-Bing,Liu, Miao-Chang,Wu, Hua-Yue
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supporting information
p. 4971 - 4975
(2019/09/30)
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- SILICON-CONTAINING COMPOUND, LIQUID-CRYSTAL COMPOSITION AND LIQUID-CRYSTAL DISPLAY USING THE SAME
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A silicon-containing compound, liquid-crystal composition and a liquid-crystal display using the silicon-containing compound are provided. The silicon-containing compound has a structure represented by Formula (I): wherein K, R1, A1,
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- C70 Fullerene-Catalyzed Metal-Free Photocatalytic ipso-Hydroxylation of Aryl Boronic Acids: Synthesis of Phenols
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A metal-free C70 fullerene-catalyzed method has been developed for the ipso-hydroxylation of aryl and heteroaryl boronic acids to corresponding phenols under photocatalytic conditions. The reaction proceeds under oxygen atmosphere and the mechanistic study revealed that C70 plays a critical role in the generation of reactive oxygen species in the presence of blue light. Reactions in the presence of 18O-labelled water and oxygen confirmed the generation of reactive oxygen species from oxygen molecule. Amine used as a reductant could be recovered in the form of imine. The current method is also applicable to the synthesis of aryl ethers in one-pot two-step process. (Figure presented.).
- Kumar, Inder,Sharma, Ritika,Kumar, Rakesh,Kumar, Rakesh,Sharma, Upendra
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supporting information
p. 2013 - 2019
(2018/04/02)
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- Oxidative 1,2-Difunctionalization of Ethylene via Gold-Catalyzed Oxyarylation
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Under the conditions of oxidative gold catalysis, exposure of ethylene to aryl silanes and alcohols generates products of 1,2-oxyarylation. This provides a rare example of a process that allows catalytic differential 1,2-difunctionalization of this feedstock chemical.
- Harper, Matthew J.,Emmett, Edward J.,Bower, John F.,Russell, Christopher A.
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supporting information
p. 12386 - 12389
(2017/09/22)
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- Phosphamide nucleosides compound, pharmaceutically acceptable salt and application thereof, and pharmaceutical composition
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The invention provides a phosphamide nucleosides compound as shown in a formula (I). Compared with the prior art, the phosphamide nucleosides compound has the advantages that the phosphamide nucleosides compound has antiviral activity which is remarkably higher than that of TAF on aspects of HIV resisting and hepatitis B resisting; the HIV resisting activity of some compounds is about 10 times higher than that of the TAF, and the hepatitis B resisting activity of the same compounds is also 2-5 times higher than that of the TAF; moreover, the phosphamide nucleosides compound has stable chemical properties and is difficult to hydrolyze by hydrolytic enzymes; compared with the TAF, the phosphamide nucleosides compound has superiority on aspect of toxicity and especially renal toxicity, and patients suffering from HIV and/or HBV can be effectively treated by the compound or isomer thereof at a low clinic dosage.
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Paragraph 0139; 0143; 0144; 0145
(2017/08/28)
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- Increased hydrophobicity and estrogenic activity of simple phenols with silicon and germanium-containing substituents
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Here, we report the systematic synthesis and characterization of simple phenols bearing a trialkyl(aryl)silyl or trialkyl(aryl)germyl functional group as a hydrophobic substituent. These silicon and germanium analogues exhibited higher hydrophobicity than
- Fujii, Shinya,Miyajima, Yu,Masuno, Hiroyuki,Kagechika, Hiroyuki
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p. 160 - 166
(2013/02/23)
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- Gold-catalyzed oxidative coupling reactions with aryltrimethylsilanes
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During continuing studies with a novel oxidative gold oxyarylation reaction, arylsilanes were found to be competent coupling partners, providing further evidence for an intramolecular electrophilic aromatic substitution mechanism. While providing yields complementary to those of the previously described boronic acid methods, the use of trimethylsilanes reduces the observation of homocoupling byproducts and allows for facile intramolecular coupling reactions.
- Brenzovich Jr., William E.,Brazeau, Jean-Francois,Toste, F. Dean
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supporting information; experimental part
p. 4728 - 4731
(2010/12/25)
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- N-heterocyclic carbene-catalyzed hydroacylation of unactivated double bonds
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(Chemical Equation Presented) An intramolecular N-heterocyclic carbene (NHC)-catalyzed hydroacylation of unactivated double bonds is reported. Systematic variation of the catalyst structure revealed an N- mesitylthiazolylidene annulated with a seven-membered ring to be especially reactive. This NHC enables a unique C-C bond-forming reaction to afford substituted chroman-4-ones in moderate to excellent yields, even ones containing all-carbon quaternary centers.
- Hirano, Keiichi,Biju, Akkattu T.,Piel, Isabel,Glorius, Frank
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supporting information; experimental part
p. 14190 - 14191
(2010/02/15)
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- COMPOUNDS FOR INHIBITING KSP KINESIN ACTIVITY
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The present invention provides compounds of Formula (I) (wherein R1, R3, X, W, Z and ring Y are as defined herein). The present invention also provides compositions comprising these compounds that are useful for treating cellular proliferative diseases or disorders associated with KSP kinesin activity and for inhibiting KSP kinesin activity.
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Page/Page column 167; 168
(2010/11/23)
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- Development of Odorless Thiols and Sulfides and Their Applications to Organic Synthesis
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Development of new odorless thiols (dodecanethiol, 4-n- heptylphenylmethanethiol, 4-trimethylsilylphenylmethanethiol, 4-trimethylsilylbenzenethiol) and an odorless sulfide (1-methylsulfanyldodecane) and their applications to dealkylation, Michael addition, Swern oxidation, and Corey-Kim oxidation are described.
- Nishide, Kiyoharu,Ohsugi, Shin-Ichi,Miyamoto, Tetsuo,Kumar, Kamal,Node, Manabu
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p. 189 - 200
(2007/10/03)
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- Synthetic equivalents of benzenethiol and benzyl mercaptan having faint smell: Odor reducing effect of trialkylsilyl group
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Syntheses and odor tests of the trialkylsilylated benzyl mercaptans and benzenethiols have revealed that the trimethylsilyl substituent on the benzene ring has a remarkable effect in reducing the foul smell of the parent benzyl mercaptan and benzenethiol.
- Nishide, Kiyoharu,Miyamoto, Tetsuo,Kumar, Kamal,Ohsugi, Shin-Ichi,Node, Manabu
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p. 8569 - 8573
(2007/10/03)
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