3558-60-9Relevant academic research and scientific papers
Intramolecular interactions in ortho-methoxyalkylphenylboronic acids and their catechol esters
Adamczyk-Wozniak, Agnieszka,Borys, Krzysztof M.,Czerwinska, Karolina,Gierczyk, Blazej,Jakubczyk, Michal,Madura, Izabela D.,Sporzynski, Andrzej,Tomecka, Ewelina
, p. 616 - 621 (2013)
(Graph Presented) Catechol esters of ortho-methoxyalkylphenylboronic acids have been synthesized and characterized by 17O NMR spectroscopy. The results were compared with the data for the parent acids. The influence of intramolecular and intermolecular hydrogen bonds on the properties of the boronic acids has been discussed. The 17O NMR data for the boronic esters proved that there are no O → B interactions in the investigated compounds. This fact is connected with weak Lewis acidity of the parent acids and their low sugars' receptors activity. Crystal structure of ortho -methoxyphenylboronic acid catechol ester was determined.
Oxidative 1,2-Difunctionalization of Ethylene via Gold-Catalyzed Oxyarylation
Harper, Matthew J.,Emmett, Edward J.,Bower, John F.,Russell, Christopher A.
supporting information, p. 12386 - 12389 (2017/09/22)
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.
Photoredox-Assisted Reductive Cross-Coupling: Mechanistic Insight into Catalytic Aryl-Alkyl Cross-Couplings
Paul, Avishek,Smith, Mark D.,Vannucci, Aaron K.
, p. 1996 - 2003 (2017/02/26)
Here, we describe a photoredox-assisted catalytic system for the direct reductive coupling of two carbon electrophiles. Recent advances have shown that nickel catalysts are active toward the coupling of sp3-carbon electrophiles and that well-controlled, light-driven coupling systems are possible. Our system, composed of a nickel catalyst, an iridium photosensitizer, and an amine electron donor, is capable of coupling halocarbons with high yields. Spectroscopic studies support a mechanism where under visible light irradiation the Ir photosensitizer in conjunction with triethanolamine are capable of reducing a nickel catalyst and activating the catalyst toward cross-coupling of carbon electrophiles. The synthetic methodology developed here operates at low 1 mol % catalyst and photosensitizer loadings. The catalytic system also operates without reaction additives such as inorganic salts or bases. A general and effective sp2-sp3 cross-coupling scheme has been achieved that exhibits tolerance to a wide array of functional groups.
Synthetic method for medical intermediate methyl phenethyl ether of metoprolol
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Paragraph 0015; 0016, (2017/03/28)
The invention discloses a synthetic method for a medical intermediate methyl phenethyl ether of metoprolol. The synthetic method includes the following steps that 1.3 mol of phenethyl alcohol (2) and 1.5-1.7 mol of sodium sulfite are added into a reaction vessel provided with a stirrer, a thermometer, a reflux condenser and a dropping funnel, the stirring speed is controlled to be 130-160 rpm, and the temperature of the solution is increased to 80-85 DEG C; 1.3-1.5 mol of methyl-trimethylamine phosphoric acid is dropwise added, and continuous reacting is carried out for 3-4 h after the methyl-trimethylamine phosphoric acid is added; 300 ml of potassium chloride solutions are added, the temperature of the solution is reduced to 3-5 DEG C, the mixture is extracted with cyclohexane 3-5 times, an extracting solution is dehydrated through a dehydrating agent, the cyclohexane is evaporated, reduced pressure distillation is carried out, and the fractions obtained at the temperature of 65-75 DEG C are collected; recrystallization is carried out in propionitrile, and the methyl phenethyl ether (1) is obtained; the mass percent of the potassium chloride solutions ranges from 15% to 20%, and the mass percent of the cyclohexane ranges from 80% to 85%.
Photocatalytic nucleophilic addition of alcohols to styrenes in Markovnikov and anti-Markovnikov orientation
Weiser, Martin,Hermann, Sergej,Penner, Alexander,Wagenknecht, Hans-Achim
, p. 568 - 575 (2015/06/08)
The nucleophilic addition of methanol and other alcohols to 1,1-diphenylethylene (1) and styrene (6) into the Markovnikov- and anti-Markovnikov-type products was selectively achieved with 1-(N,N-dimethylamino)pyrene (Py) and 1,7-dicyanoperylene-3,4:9,10-tetracarboxylic acid bisimide (PDI) as photoredox catalysts. The regioselectivity was controlled by the photocatalyst. For the reductive mode towards the Markovnikov-type regioselectivity, Py was applied as photocatalyst and triethylamine as electron shuttle. This approach was also used for intramolecular additions. For the oxidative mode towards the anti-Markovnikov-type regioselectivety, PDI was applied together with Ph-SH as additive. Photocatalytic additions of a variety of alcohols gave the corresponding products in good to excellent yields. The proposed photocatalytic electron transfer mechanism was supported by detection of the PDI radical anion as key intermediate and by comparison of two intramolecular reactions with different electron density. Representative mesoflow reactor experiments allowed to significantly shorten the irradiation times and to use sunlight as "green"light source.
METHOD FOR PRODUCING ETHER COMPOUND
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Paragraph 0141, (2015/01/18)
An object of the present invention is to provide a method for producing an ether compound easily in a small number of steps at lower costs in high yields. The present invention relates to a method in which the ether compound represented by the general formula (1) is produced by reacting the specific carbonyl compound specified in the general formula (2) and the specific dialkoxy compound specified in the general formula (3) with hydrogen in the presence of a hydrogenation catalyst and an acidic substance to perform hydrogenation.
Cross-coupling of alkyl halides with aryl or alkyl Grignards catalyzed by dinuclear Ni(ii) complexes containing functionalized tripodal amine-pyrazolyl ligands
Xue, Fei,Zhao, Jin,Hor, T. S. Andy
, p. 5150 - 5158 (2013/04/10)
Structurally distinctive dinuclear Ni(ii) complexes with furan or thiophene tethered amine-pyrazolyl tripodal hybrid ligands have been synthesized and crystallographically characterized. All complexes are catalytically active towards cross-coupling of aryl/alkyl Grignard reagents with β-H containing alkyl halides at room temperature in the presence of N,N,N',N'- tetramethylethylenediamine (TMEDA). The catalytic efficacy of the complexes is dependent on the tether substituent at the central amine. Two species, Ni(ii) TMEDA and Mg(ii) TMEDA complexes, have been isolated from the catalytic reaction mixtures under different conditions. Some ligand-stabilized Ni(ii) and Mg(ii) bimetallic species have also been identified in the ESI-MS spectra.
Iron-catalyzed N-alkylation using π-activated ethers as electrophiles
Fan, Xiaohui,Fu, Lin-An,Li, Na,Lv, Hao,Cui, Xiao-Meng,Qi, Yuan
supporting information, p. 2147 - 2153 (2013/04/10)
A new method for the synthesis of diverse N-alkylation compounds was developed via an iron-catalyzed etheric Csp3-O cleavage with the C-N bond formation in the reaction of π-activated ethers with various nitrogen-based nucleophiles. In addition, the mechanism of this reaction was investigated. The Royal Society of Chemistry 2013.
Fe-promoted cross coupling of homobenzylic methyl ethers with Grignard reagents via sp3 C-O bond cleavage
Luo, Shuang,Yu, Da-Gang,Zhu, Ru-Yi,Wang, Xin,Wang, Lei,Shi, Zhang-Jie
supporting information, p. 7794 - 7796 (2013/09/02)
The first iron-catalyzed formal cross coupling of homobenzylic methyl ethers with alkyl Grignard reagents is realized. The reaction is proposed to proceed through a sequence of dehydroalkoxylation to form the vinyl-intermediate, followed by Fe-catalyzed selective carbometalation to form a benzylic Grignard reagent.
Easy eco-friendly phenonium ion production from phenethyl alcohols in dimethyl carbonate
Barontini,Proietti Silvestri,Nardi,Bovicelli,Pari,Gallucci,Spezia,Righi
supporting information, p. 5004 - 5006 (2013/08/28)
An efficient and simple one-pot procedure for selective etherification of 2-aryl-ethylalcohols has been achieved through Amberlyst 15-catalyzed reaction in dimethyl carbonate (DMC). Moreover, the polymer catalyst could be recovered and reused with no effect on its activity. The reaction mechanism involves the formation of phenonium ion which has been demonstrated by a C-C bond forming reaction. Theoretical studies are in agreement with and thus explain experimental results.
