- Size-selective catalysts in five functionalized porous coordination polymers with unsaturated zinc centers
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The five reported structural isomorphic porous coordination polymers (PCPs) 1-5, namely, [Zn(L)(ip) (1), Zn(L)(aip) (2), Zn(L)(hip) (3), Zn(L)(nip) (4), and Zn(L)(HBTC) (5) (L = N4,N4′-di(pyridine-4-yl)biphenyl-4,4′-dicarboxamide, H2ip = isophthalic acid, H2aip = 5-aminoisophthalic acid, H2hip = 5-hydroxyisophthalic acid, H2nip = 5-nitroisophthalic acid, H3BTC = 1,3,5-benzenetricarboxylic acid)] were used to catalyze the acetylation of phenol. All these heterogeneous catalysts exhibit good catalytic efficiency and size-selectivity toward the acetylation of phenols owing to their unsaturated metal centers, non-coordinated amide, and suitable channel size and shape. Among them, 2 displays the highest catalytic activity and excellent cooperative catalysis due to the presence of basic non-coordinated amide groups.
- Deng, Dongsheng,Guo, Hui,Ji, Baoming,Wang, Weizhou,Ma, Lufang,Luo, Feng
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- Structure-activity relationship on human serum paraoxonase (PON1) using substrate analogues and inhibitors
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Substrate analogues based on the parent compounds paraoxon and phenyl acetate were tested on human serum paraoxonase (PON1) to explore the active site of the enzyme. Replacement of the nitro group of paraoxon with an amine or hydrogen, as well as electronic changes to the parent compound, converted these analogues into inhibitors. Introduction of either electron-withdrawing or donating groups onto phenyl acetate resulted in reduction in their rate of hydrolysis by PON1.
- Bargota, Rakesh S.,Akhtar, Mahmoud,Biggadike, Keith,Gani, David,Allemann, Rudolf K.
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- A New and Selective Metal-Catalyzed Baeyer-Villiger Oxidation Procedure
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A new, highly selective and high yielding procedure is described for the Baeyer-Villiger oxidation, using a tin-catalyst and bis(trimethylsilyl) peroxide (BTP).
- G?ttlich, Richard,Yamakoshi, Koichi,Sasai, Hiroaki,Shibasaki, Masakatsu
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- Use of Molecular Oxygen in the Baeyer-Villiger Oxidation The Influence of Metal Catalysts
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Baeyer-Villiger oxidation of ketones using molecular oxygen and benzaldehyde in the absence of metal catalysts afforded lactones in high yields.The catalytic activity of various metal salts has been studied.Key Words: Baeyer-Villiger oxidation, Molecular
- Bolm, Carsten,Schlingloff, Gunther,Weickhardt, Konrad
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- Ligand-Promoted Palladium-Catalyzed C?H Acetoxylation of Simple Arenes
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The palladium-catalyzed C?H oxidation of simple arenes is an attractive strategy to obtain phenols, which have many applications in the fine chemicals industry. Although some advances have been made in this research area, low reactivity and selectivity are, in general, observed. This report describes a new catalytic system for the efficient C?H acetoxylation of simple arenes based on Pd(OAc)2 and a pyridinecarboxylic acid ligand.
- Valderas, Carolina,Naksomboon, Kananat,Fernández-Ibá?ez, M. ángeles
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- Electron-transfer Chain (ETC) Promotion of Aromatic Substitution Reactions. Entry into the SON2 Mechanism via Ipso Radical Attack
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The oxidative electron-transfer chain mechanism, the SON2 mechanism, is shown to be initiated by benzoyl-oxyl radicals, since 4-fluoroanisole can be converted into a mixture of 4-methoxyphenyl acetate and benzoate (maximum ratio 10:1) in high yield by decomposing benzoyl peroxide in HOAc-KOAc at 78 deg C.
- Eberson, Lennart,Joensson, Lennart
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- Electrophilic components in the electrochemical acetoxylation of substituted arenes
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The mechanism of anodic acetoxylation of substituted arenes under conditions of undivided galvanostatic electrolysis in MeCN containing acetate is suggested and an important role of electrophilic components (AcOH or ZnCl2) catalyzing transformation of intermediate ipso-acetoxylated polysubstituted arenonium cations to corresponding ortho-acetoxylated arenonium cations, which give acetoxylation products after deprotonation, is experimentally proved.
- Burasov, Alexander V.,Petrosyan, Vladimir A.
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- Acetylation of phenols in organic solvent catalyzed by a lipase from chromobacterium viscosum
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Lipase from Chromobacterium viscosum, absorbed on an inert support, was employed as catalyst for the esterification of monohydric phenols in organic solvent, with vinyl acetate as acyl donor. The effect of aromatic ring substitution on the initial rate of transesterification was investigated.
- Nicolosi,Piatelli,Sanfilippo
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- Bacteriogenic iron oxide as an effective catalyst for Baeyer-Villiger oxidation with molecular oxygen and benzaldehyde
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Iron oxide produced by iron-oxidizing bacteria, Leptothrix ochracea, (L-BIOX) obtained from a freshwater purification plant, Joyo City in Kyoto, Japan catalyzed Baeyer-Villiger oxidation with molecular oxygen in the presence of benzaldehyde at 25 °C more efficiently than usual iron compounds. L-BIOX can promote the reactions of various substrates to give the desired products in sufficient yields and was found to be reusable. Scanning transmission electron microscopy and 57Fe M?ssbauer spectroscopy revealed that no change of the surface structure of L-BIOX was observed even after four times of the recycling test and the oxidation state of iron in L-BIOX is trivalent before and after the oxidation of cyclohexanone. An investigation with analogous amorphous iron oxides which contain silicon revealed that the catalytic activity of L-BIOX might stem from a synergetic effect of iron and silicon in the structure.
- Mandai, Kyoko,Hanata, Minae,Mitsudo, Koichi,Mandai, Hiroki,Suga, Seiji,Hashimoto, Hideki,Takada, Jun
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- Substituent Effect in o-Nitroperbenzoic Acid Oxidation of m- and p-Substituted Acetophenones
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The Baeyer-Villiger reaction of m- and p-substituted acetophenones (substituents: H, p-MeO, p-t-Bu, p-i-Pr, p-Et, p-Me, p-Cl, p-Br, m-MeO, m-Me, m-Cl) with o-nitroperbenzoic acid was studied in chloroform at 30 deg C.The rate constants for the general acid catalysis were measured at several concentrations of o-nitrobenzoic acid which acted as an acid catalyst.The uncatalyzed and acid-catalyzed rate constants obtained afforded ρ values of -2.16 and -4.11 with ?, respectively.The results indicated that the rate-determining step is the migration of the phenyl group in the peroxy acid-carbonyl adduct for all the substituents studied, whether the reaction is acid-catalyzed or not, and that the acid catalyst intervenes only in the formation of the acid-ketone adduct in the initial state and not in the migration step.The variation of the leaving group abilities required the variation of the substituent constants applied, whereas the acid intervention in the addition step was reflected only in the variation of the ρ value, not in the substituent constants to be applied.The smaller resonance demand for o-nitrobenzoic acid indicated that the structure of the transition state in the migration step was looser and that the position of the transition state was earlier than those for m-chloroperbenzoic acid.
- Token, Katsuo,Hirano, Kenji,Yokoyama, Tai,Goto, Katsumi
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- Potassium tris(triflyl)methide (KCTf3): A broadly applicable promoter for cationic metal catalysis
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KCTf3, a commercially available, easily handled neutral salt, enhanced the reaction rates and the chemical yields of a wide spectrum of cationic metal catalyzed reactions, ranging from traditional Lewis acid catalysis to transition metal catalysis.
- Han, Junbin,Lu, Zhichao,Wang, Weibo,Hammond, Gerald B.,Xu, Bo
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- Noncross-linked polystyrene nanoencapsulation of ferric chloride: A novel and reusable heterogeneous macromolecular Lewis acid catalyst toward selective acetylation of alcohols, phenols, amines, and thiols
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Ferric chloride has been successfully nanoencapsulated for the first time on a non-cross-linked polystyrene matrix as the shell material via the coacervation technique. The resulting polystyrene nanoencapsulated ferric chloride was used as a novel and rec
- Alinejad, Sara,Donyapeyma, Ghazaleh,Rahmatpour, Ali
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- Preparation process of 2-bromo-4-hydroxy anisole
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The invention relates to a preparation process of 2-bromo-4-hydroxy anisole. The preparation process comprises the following steps: reacting 4-hydroxy anisole with acetyl chloride in an organic alkalisolution at low temperature to generate 4-acetyl anisol
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Paragraph 0024; 0026-0027
(2021/02/20)
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- Direct Acetoxylation of Arenes
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Acetoxylation of arenes is an important reaction and an unmet need in chemistry. We report a metal-free, direct acetoxylation reaction using sodium nitrate under an anhydrous environment of trifluoroacetic acid, acetic acid, and acetic anhydride. Arenes (31 examples), with oxidation potentials (Eox, in V vs SCE) lower than benzene (2.48 V), were acetoxylated with good yields and regioselectivity. A stepwise, single electron-transfer mechanism is proposed.
- Hong Nguyen, Thi Anh,Hou, Duen-Ren
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supporting information
p. 8127 - 8131
(2021/08/23)
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- Novel p-functionalized chromen-4-on-3-yl chalcones bearing astonishing boronic acid moiety as MDM2 inhibitor: Synthesis, cytotoxic evaluation and simulation studies
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Background: Novel 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenyl-boronic acid derivatives (5a-h) as well as other 6/7/8-substituted-3-(3-oxo-3-(4-substituted-phenyl)prop-1-enyl)-4H-chromen-4-one derivatives (3a-u) have been designed as p53-MDM2 pathway inhibitors and reported to possess significant cytotoxic properties against several cancer cell lines. Objectives: The current project aims to frame the structure-anticancer activity relationship of chromen-4-on-3-yl chalcones (3a-u/5a-h). In addition, docking studies were performed on these chromeno-chalcones in order to have an insight into their interaction possibilities with MDM2 pro-tein. Methods: Twenty-nine chromen-4-on-3-yl chalcone derivatives (3a-u/5a-h) were prepared by utilizing silica supported-HClO4 (green route with magnificent yield) and tested against four cancer cell lines (HCT116, MCF-7, THP-1, NCIH322). Results: Among the series 3a-u, compound 3b exhibited the highest anticancer activity (with IC50 values ranging from 8.6 to 28.4 μM) overall against tested cancer cell lines. Interestingly, para-Boronic acid derivative (5b) showed selective inhibition against colon cancer cell line, HCT-116 with an IC50 value of 2.35 μM. Besides the emblematic hydrophobic interactions of MDM2 inhibi-tors, derivative 5b was found to exhibit extra hydrogen bonding with GLN59 and GLN72 residues of MDM2 in molecular dynamics (MD) simulation. All the compounds were virtually nontoxic against normal fibroblast cells. Conclusion: Novel compounds were obtained with good anticancer activity especially 6-Chlorochromen-4-one substituted boronic acid derivative 5b. The molecular docking study proposed good activity as a MDM-2 inhibitor suggesting hydrophobic as well as hydrogen bonding interactions with MDM2.
- Bhatia, Richa Kaur,Coutinho, Evans C.,Garg, Ruchika,Kancherla, Satyavathi,Kaur, Maninder,Madan, Jitender,Pissurlenkar, Raghuvir R. S.,Singh, Lakhwinder,Yadav, Manmohan
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p. 212 - 228
(2020/03/10)
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- Copper-Catalyzed Acetylation of Electron-Rich Phenols and Anilines
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An approach has been developed for the copper-catalyzed acetylation of phenols and anilines with potassium thioacetate as an acetylating reagent. Although only electron-rich phenols and anilines are compatible with this protocol, the reaction can provide moderate to high yields under mild conditions. Compared with other acetylating reagents, the current reagent has certain advantages, such as its low cost, easy availability, stability, insensitivity to water or air, and ease of storage.
- Zhang, Jieyu,Ke, Qiumin,Tian, Feitao,Jiang, Bei,Ji, Chang-An,Zhang, Lingling,Yu, Jian,Huang, Dayun,Yan, Guobing
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supporting information
p. 726 - 730
(2019/03/26)
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- Evaluating Gold and Selenium Chemistry for Selective Transformations of Lignin Model Compounds
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Applications of gold and selenium chemistry are reported as novel approaches to promote lignin depolymerization into more valuable chemicals via selective oxidation reactions (alcohol oxidations and Baeyer-Villiger reactions). In this study, we proposed two different oxidative methodologies using Au/SiO2 and phenylseleninic acid resin (PAR) as stable and reusable catalysts to promote selective transformations of the β-O-4 linkage of lignin model compounds. After evaluating the catalytic systems under batch conditions, they were both applied in a packed-bed reactor for continuous flow operations. By using Au/SiO2 as a catalyst under flow conditions, ketones were efficiently obtained (up to 86% conversion) from the oxidation of alcohols with a residence time (tR) of 30 min. In the case of Baeyer-Villiger oxidations catalyzed by phenylseleninic acid resin, the corresponding esters were obtained in up to 91% conversion (tR=30 min). Both systems efficiently catalyzed the conversion of the lignin model compounds. (Figure presented.).
- Santos, Wagner C. C.,Dias, Kevin A.,Santos, Leidaiany P.,Kisukuri, Camila M.,Rodrigues, Thenner S.,Geonmonond, Rafael S.,Camargo, Pedro H. C.,Andrade, Leandro H.
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p. 1376 - 1383
(2018/02/13)
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- Copper-Catalyzed C-S Bond Formation via the Cleavage of C-O Bonds in the Presence of S8 as the Sulfur Source
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Useful and applicable methods for one-pot and odorless synthesis of unsymmetrical and symmetrical diaryl sulfides via C-O bond activation are presented. First, a new efficient procedure for the synthesis of unsymmetrical sulfides using the cross-coupling reaction of phenolic esters such as acetates, tosylates, and triflates and with arylboronic acid or triphenyltin chloride as the coupling partners is reported. Depending on the reaction, S 8 /KF or S 8 /NaO t -Bu system is found to be an effective source of sulfur in the presence of copper salts and in poly(ethylene glycol) as a green solvent. Then, the synthesis of symmetrical diaryl sulfides from phenolic compounds by using S 8 as the sulfur source and NaO t -Bu in anhydrous DMF at 120 °C under N 2 is described. By these protocols, the synthesis of a variety of unsymmetrical and symmetrical sulfides become easier than the available protocols in which thiols and aryl halides are directly used for the preparation of the sulfides.
- Rostami, Abed,Rostami, Amin,Ghaderi, Arash,Gholinejad, Mohammad,Gheisarzadeh, Sajedeh
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p. 5025 - 5038
(2017/10/06)
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- Isopropenyl acetate: A cheap and general acylating agent of alcohols under metal-free conditions
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Functionalized primary, secondary and tertiary alcohols are efficiently acetylated by isopropenyl acetate and catalytic p-TsOH.
- Temperini, Andrea,Minuti, Lucio,Morini, Tommaso,Rosati, Ornelio,Piazzolla, Francesca
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p. 4051 - 4053
(2017/09/27)
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- Regioselective Baeyer-Villiger oxidation of lignin model compounds with tin beta zeolite catalyst and hydrogen peroxide
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Lignin depolymerization represents a promising approach to the sustainable production of aromatic molecules. One potential approach to the stepwise depolymerization of lignin involves oxidation of the benzylic alcohol group in β-O-4 and β-1 linkages, followed by Baeyer-Villiger oxidation (BVO) of the resulting ketones and subsequent ester hydrolysis. Towards this goal, BVO reactions were performed on 2-adamantanone, a series of acetophenone derivatives, and lignin model compounds using a tin beta zeolite/hydrogen peroxide biphasic system. XRD, 119Sn MAS NMR spectroscopy, DRUVS and XPS were used to determine tin speciation in the catalyst, the presence of both framework Sn and extra framework SnO2 being inferred. Conversion of ketones to BVO products was affected by electron donation as well as steric hindrance, 4′-methoxyacetophenone affording the highest yield of ester (81%). As the size and complexity of the ketone increased, excess hydrogen peroxide was typically needed for successful BVO. Yields of ester products derived from β-O-4 and β-1 lignin models were modest due to the formation of polymeric material stemming from direct ring hydroxylation.
- Jennings, John A.,Parkin, Sean,Munson, Eric,Delaney, Sean P.,Calahan, Julie L.,Isaacs, Mark,Hong, Kunlun,Crocker, Mark
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p. 25987 - 25997
(2017/07/07)
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- Continuous Production of Biorenewable, Polymer-Grade Lactone Monomers through Sn-Β-Catalyzed Baeyer–Villiger Oxidation with H2O2
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The Baeyer–Villiger oxidation is a key transformation for sustainable chemical synthesis, especially when H2O2 and solid materials are employed as oxidant and catalyst, respectively. 4-substituted cycloketones, which are readily available from renewables, present excellent platforms for Baeyer–Villiger upgrading. Such substrates exhibit substantially higher levels of activity and produce lactones at higher levels of lactone selectivity at all values of substrate conversion, relative to non-substituted cyclohexanone. For 4-isopropyl cyclohexanone, which is readily available from β-pinene, continuous upgrading was evaluated in a plug-flow reactor. Excellent selectivity (85 % at 65 % conversion), stability, and productivity were observed over 56 h, with over 1000 turnovers (mol product per mol Sn) being achieved with no loss of activity. A maximum space–time yield that was almost twice that for non-substituted cyclohexanone was also obtained for this substrate [1173 vs. 607 g(product) kg(catalyst)?1 cm?3 h?1]. The lactone produced is also shown to be of suitable quality for ring opening polymerization. In addition to demonstrating the viability of the Sn-β/H2O2 system to produce renewable lactone monomers suitable for polymer applications, the substituted alkyl cyclohexanones studied also help to elucidate steric, electronic, and thermodynamic elements of this transformation in greater detail than previously achieved.
- Yakabi, Keiko,Mathieux, Thibault,Milne, Kirstie,López-Vidal, Eva M.,Buchard, Antoine,Hammond, Ceri
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p. 3652 - 3659
(2017/09/13)
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- A synthesizing methyl emulsion method of alkali
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The invention provides a synthetic method for methyl caulophine. The method comprises the following steps: with isovanillin and p-hydroxyanisole as raw materials, successively subjecting isovanillin to bromination and methylation so as to obtain 2-bromo-3
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Paragraph 0043; 0044
(2016/10/10)
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- DMAP-based flexible polymer networks formed via Heck coupling as efficient heterogeneous organocatalysts
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Two DMAP-based flexible polymer networks TPB-DMAP and TPA-DMAP have been successfully synthesized via palladium catalyzed Heck cross-coupling. The structures of these polymers were confirmed by solid state 13C CP/MAS and Fourier transform infrared spectroscopy (FTIR). Although both polymers have negligible surface areas, they exhibit excellent catalytic efficiency for the acylation of 1-phenylethanol with acetic anhydride due to their good swelling capacities. Utilized as a typical catalyst, the polymer TPA-DMAP shows high activities for acylation of a variety of alcohols to the corresponding esters. Moreover, the catalyst can be recycled at least ten times without obvious loss of catalytic activity.
- Xu, Wei,Xia, Wu,Guan, Yukun,Wang, Yiming,Lu, Cuifen,Yang, Guichun,Nie, Junqi,Chen, Zuxing
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- Synthesis, structure and multifunctional catalytic properties of a Cu(i)-coordination polymer with outer-hanging CuBr2
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A 1D Cu(i)-coordination polymer [(CuL1)(CuBr2), 1] carrying external copper bromide moieties was synthesized. The outer-hanging [CuBr2]- moiety is attached to the 1D Cu(i)-CP backbone via a Cu?Cu bonding interaction, which makes it look like a coordination polymer supported CuBr2 species. 1 exhibits excellent multifunctional catalytic activity for phenol acetylation, A3-coupling (aldehyde-alkyne-amine) and styrene oxide methanolysis reactions. Its heterogeneous catalytic nature was confirmed by solution leaching experiment and it can be reused without significant loss of its catalytic activity and selectivity for the above reactions.
- Zhu, Neng-Xiu,Zhao, Chao-Wei,Yang, Jing,Wang, Xue-Ru,Ma, Jian-Ping,Dong, Yu-Bin
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p. 108645 - 108653
(2016/11/30)
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- Highly efficient and recyclable acetylation of phenols and alcohols by nickel zirconium phosphate under solvent-free conditions
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Nickel zirconium phosphate nanoparticles have been used as an efficient catalyst for the acetylation of a wide range of alcohols and phenols with acetic anhydride in good to excellent yields under solvent-free conditions. The steric and electronic properties of the different substrates had a significant influence on the reaction conditions required to achieve the acetylation. The catalyst used in the current study was characterized by inductively coupled plasma optical emission spectroscopy, X-ray diffraction, N2 adsorption-desorption, scanning electron microscopy, and transmission electron microscopy. This nanocatalyst could also be recovered and reused at least six times without any discernible decrease in its catalytic activity.
- Hajipour, Abdol Reza,Karimi, Hirbod,Kohi, Afshin
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- Photochemistry of aroyloxiranes: Substituent effect on oxepinones and hydroxyalkenones formation
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The photo-irradiation of some aroyloxiranes with Pyrex filtered UV-light from 125?W medium pressure Hg lamp has been described. These compounds furnished the 2-aryl-4,10-dihydrofuro[3,2-c][1]benzoxepin-10-ones and the hydroxyalkenones by the photochemical irradiation. The product(s) formation/distribution in terms of oxepinones and the hydroxyalkenones largely depended upon the nature of the substituent: the oxiranes having electron-donating groups in their benzoyl moiety gave the hydroxyalkenones while oxiranes having electron-withdrawing groups furnished the oxepinones as the major products. The formation of oxepinones has been envisaged to occur through the heterolytic [Formula presented] bond cleavage of epoxide to give carbonyl ylide intermediates followed by the furo-oxepinone ring formation via [3+2] cycloaddition and of hydroxyalkenones through the initial β-H abstraction followed by epoxide ring opening. The structures of all the compounds (substrates and photoproducts) have been determined on the basis of their spectral data (IR, NMR and Mass).
- Dalal, Aarti,Khanna, Radhika,Berar, Urmila,Kamboj, Ramesh C.
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p. 238 - 245
(2016/07/22)
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- Exceptional activity of gallium(III) chloride and chlorogallate(III) ionic liquids for Baeyer–Villiger oxidation
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Baeyer–Villiger oxidation of cyclic ketones, using H2O2 as the oxidising agent, was systematically studied using a range of metal chlorides in different solvents, and in neat chlorogallate(III) ionic liquids. The extremely high activity of GaCl3 in promoting oxidation with H2O2, irrespective of solvent, was reported for the first time. The activity of all other metal chlorides was strongly solvent-dependent. In particular, AlCl3 was very active in a protic solvent (ethanol), and tin chlorides, SnCl4 and SnCl2, were active in aprotic solvents (toluene and dioxane). In order to eliminate the need for volatile organic solvent, a Lewis acidic chlorogallate(III) ionic liquid was used in the place of GaCl3, which afforded typically 89–94% yields of lactones in 1–120 min, at ambient conditions. Raman and 71Ga NMR spectroscopic studies suggest that the active species, in both GaCl3 and chlorogallate(III) ionic liquid systems, are chlorohydroxygallate(III) anions, [GaCl3OH], which are the products of partial hydrolysis of GaCl3 and chlorogallate(III) anions; therefore, the presence of water is crucial.
- Markiton, Magdalena,Chrobok, Anna,Matuszek, Karolina,Seddon, Kenneth R.,Swadzba-Kwasny, Ma?gorzata
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p. 30460 - 30467
(2019/01/14)
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- Acetylation of alcohols and phenols under solvent-free conditions using iron zirconium phosphate
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Iron zirconium phosphate (ZPFe) nanoparticles were found to function as an efficient catalyst for the acetylation of a wide range of alcohols and phenols using acetic anhydride, generating good to excellent yields under solvent-free conditions. The steric and electronic properties of various substrates had a significant influence on the reaction conditions required to achieve the acetylation. The catalyst used in the current study was characterized by inductively coupled plasma-optical emission spectrometry, X-ray diffraction, N2 adsorption-desorption, scanning electron microscopy, and transmission electron microscopy. These analyses revealed that the interlayer distance in the catalyst increased from 7.5 to 9.3 ? when Fe3+ was intercalated between the layers, whereas the crystallinity of the material was reduced. This nanocatalyst could also be recovered and reused at least six times without any discernible decrease in its catalytic activity. This new method for the acetylation of alcohols and phenols has several important advantages, including mild and environmentally friendly reaction conditions, as well as good to excellent yields and a facile work-up.
- Hajipour, Abdol R.,Karimi, Hirbod,Masti, Amir
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p. 595 - 602
(2015/09/28)
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- Tribromoisocyanuric acid (TBCA) as a mild and metal free catalyst for the acetylation and formylation of hydroxyl groups under solvent free conditions
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A convenient approach for acetylation and formylation of various types of alcohols and phenols with acetic anhydride and formic acid in the presence of Tribromoisocyanuric acid (TBCA) as catalyst is reported. The reactions were carried out under solvent-free condition and in good to high yields at room temperature. This present method is featured with relatively mild reaction conditions, simple operation, broad substrate scope, clean work-up, short reaction times, good to high yields, excellent selectivity and also avoids tedious purifications and the use of toxic reagents.
- Hekmatian, Zahra,Khazaei, Ardeshir
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p. 1565 - 1570
(2016/01/26)
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- Magnetically separable γ-Fe2O3 nanoparticles: An efficient catalyst for acylation of alcohols, phenols, and amines using sonication energy under solvent free condition
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This paper reports a facile synthesis of magnetically separable iron oxide (γ-Fe2O3) nanoparticles using thermolysis method. The structural and morphological study of the synthesized γ-Fe2O3 nanoparticles was carried out using X-ray diffraction (XRD), field emission gun-scanning electron microscopy (FEG-SEM), energy dispersive X-ray spectrum (EDS), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), and X-ray photoelectron spectroscopy (XPS) techniques. The electron microscopy reveals that the γ-Fe2O3 nanoparticles have spherical morphology with a particle size in the range of 40-100 nm. The XPS study confirmed the Fe is in +3 oxidation state. The synthesized γ-Fe2O3 nanoparticles have been used as an efficient heterogeneous catalyst for the organic transformation between phenols, alcohols, and amines with acetic anhydride under sonication using mild reaction conditions. Various electrons withdrawing and electrons donating substrates show an excellent yield of desired products with the advantage of magnetic separation and reusability of γ-Fe2O3 nanocatalyst.
- Bhosale, Manohar A.,Ummineni, Divya,Sasaki, Takehiko,Nishio-Hamane, Daisuke,Bhanage, Bhalchandra M.
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- Chelating Bis-N-heterocyclic Carbene-Palladium(II) Complexes for Oxidative Arene C-H Functionalization
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Bis-N-heterocyclic carbene (NHC)-chelated palladium(II) complexes have been synthesized, characterized fully including single-crystal X-ray structural analyses, and utilized for the first time toward catalytic oxidative C-H functionalization of arenes with PhI(OAc)2 and N-bromosuccinimide. (Figure Presented).
- Desai, Sai Puneet,Mondal, Moumita,Choudhury, Joyanta
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p. 2731 - 2736
(2015/06/30)
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- The Baeyer-Villiger oxidation versus aromatic ring hydroxylation: Competing organic peracid oxidation mechanisms explored by multivariate modelling of designed multi-response experiments
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Peroxy acids can be used as the terminal oxidant for the Baeyer-Villiger oxidation of acetophenones and for direct ring hydroxylation of methoxy-substituted benzenes. An oxidative system involving 3-chloroperbenzoic acid (mCPBA) and 2,6-dimethoxyacetophenone as model substrate was investigated by means of statistical experimental design, multivariate modelling and response surface methodology. The outcome of the organic peracid oxidation experiments was portrayed by a multi-response matrix consisting of the yields of three different compounds; 2,6-dimethoxyphenyl acetate, 1-(4-hydroxy-2,6-dimethoxy-phenyl)ethanone and 3-hydroxy-2,6-dimethoxy-phenyl acetate. The optimized reaction protocol was utilized to investigate a series of various substituted acetophenones. The overall investigation revealed that both the molecular structure of the acetophenone substrate and the experimental conditions exhibited a substantial impact on whether the oxidation reaction follows the oxygen insertion or direct ring hydroxylation mechanism. An improved protocol for the direct ring hydroxylation was also obtained from the experimental and modelling described herein.
- Gambarotti, Cristian,Bj?rsvik, Hans-René
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p. 619 - 628
(2015/09/28)
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- The first vinyl acetate mediated organocatalytic transesterification of phenols: A step towards sustainability
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The present report outlines our efforts toward a simple yet elegant protocol for O-acylation of a wide variety of phenols. This highly enabling and solventless method relies on vinyl acetate as an innocuous acyl donor and DABCO as an organocatalyst. Operational simplicity, excellent yields, higher and faster conversion rates without excess reagents, a simple workup and essentially no need of columns are some of the salient features of the reported protocol.
- Kumar, Manoj,Bagchi, Sourav,Sharma, Anuj
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supporting information
p. 8329 - 8336
(2015/11/10)
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- Zinc triflate catalyzed acylation of alcohols, phenols, and thiophenols
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An expedient procedure for the acylation of alcohols, phenols, and thiophenols using catalytic amount of Zn(OTf)2 is described. This procedure is highly suitable for industrial application due to use of less toxic metal as a part of catalyst, short reaction time at ambient temperature, without any racemization of chiral alcohols.
- Kumar, N. Uday,Reddy, B. Sudhakar,Reddy, V. Prabhakar,Bandichhor, Rakeshwar
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supporting information
p. 910 - 912
(2014/02/14)
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- Zinc triflate catalyzed acylation of alcohols, phenols, and thiophenols
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An expedient procedure for the acylation of alcohols, phenols, and thiophenols using catalytic amount of Zn(OTf)2 is described. This procedure is highly suitable for industrial application due to use of less toxic metal as a part of catalyst, short reaction time at ambient temperature, without any racemization of chiral alcohols.
- Uday Kumar,Sudhakar Reddy,Prabhakar Reddy,Bandichhor, Rakeshwar
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supporting information
p. 910 - 912
(2015/02/19)
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- Synthesis, characterization and application of poly(N,N'-dibromo- Nethylnaphthyl-2,7-disulfonamide) as an efficient catalyst for the acetylation and deacetylation reactions
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In this work, a novel polymer namely poly(N,N'-dibromo-N-ethylnaphthyl-2,7- disulfonamide) (PBNS) is synthesized and characterized by studying its IR, 1H NMR, 13C NMR and thermal gravimetric analysis (TGA). This polymer is utilized as a highly efficient, heterogeneous and recyclable N-bromo reagent to catalyze acetylation of various compounds such as alcohols, phenols, thiol and amine with acetic anhydride under solvent-free conditions, and also it worthily catalyzes deacetylation of acetate esters in aqueous media.
- Khazaei, Ardeshir,Saednia, Shahnaz,Roshani, Liela,Kazem-Rostami, Masoud,Zare, Abdolkarim
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p. 159 - 167
(2014/05/20)
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- Acetylation of alcohols and phenols under solvent-free conditions using copper zirconium phosphate
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Copper zirconium phosphate nanoparticles have been used as an efficient catalyst for the acetylation of a wide range of alcohols and phenols with acetic anhydride in good to excellent yields under solvent-free conditions. The steric and electronic properties of the different substrates had a significant influence on the reaction conditions required to achieve the acetylation. The catalyst used in the current study was characterized by inductively-coupled plasma optical emission spectroscopy, energy dispersive spectroscopy, X-ray diffraction, N2 adsorption-desorption, scanning electron microscopy, and transmission electron microscopy. These analyses revealed that the interlayer distance in the catalyst increased from 7.5 to 8.0 ? when Cu2+ was intercalated between the layers, whereas the crystallinity of the material was reduced. This nanocatalyst could also be recovered and reused at least six times without any discernible decrease in its catalytic activity. This new method for the acetylation of alcohols and phenols has several key advantages, including mild and environmentally friendly reaction conditions, as well as good to excellent yields and a facile work-up.
- Hajipour, Abdol R.,Karimi, Hirbod
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p. 1982 - 1989
(2015/09/28)
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- Synthesis and biological evaluation of 4-(1,2,3-triazol-1-yl)coumarin derivatives as potential antitumor agents
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In this research, a series of 4-(1,2,3-triazol-1-yl)coumarin conjugates were synthesized and their anticancer activities were evaluated in vitro against three human cancer cell lines, including human breast carcinoma MCF-7 cell, colon carcinoma SW480 cell and lung carcinoma A549 cell. To increase the biological potency, structural optimization campaign was conducted focusing on the C-4 position of 1,2,3-triazole and the C-6, C-7 positions of coumarin. In addition, to further evaluate the role of 1,2,3-triazole and coumarin for antiproliferative activity, 9 compounds possessing 4-(piperazin-1-yl)coumarin framework and 3 derivatives baring quinoline core were also synthesized. By MTT assay in vitro, most of the compounds display attractive antitumor activities, especially 23. Further flow cytometry assays demonstrate that compound 23 exerts the antiproliferative role through arresting G2/M cell-cycle and inducing apoptosis.
- Zhang, Wenjuan,Li, Zhi,Zhou, Meng,Wu, Feng,Hou, Xueyan,Luo, Hao,Liu, Hao,Han, Xuan,Yan, Guoyi,Ding, Zhenyu,Li, Rui
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supporting information
p. 799 - 807
(2014/02/14)
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- On the synthesis, characterization and reactivity of n-heteroaryl-boryl radicals, a new radical class based on five-membered ring ligands
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The synthesis and physical characterization of a new class of N-heterocycle-boryl radicals is presented, based on five membered ring ligands with a N(sp2) complexation site. These pyrazole-boranes and pyrazaboles exhibit a low bond dissociation energy (BDE; B-H) and accordingly excellent hydrogen transfer properties. Most importantly, a high modulation of the BDE(B-H) by the fine tuning of the N-heterocyclic ligand was obtained in this series and could be correlated with the spin density on the boron atom of the corresponding radical. The reactivity of the latter for small molecule chemistry has been studied through the determination of several reaction rate constants corresponding to addition to alkenes and alkynes, addition to O 2, oxidation by iodonium salts and halogen abstraction from alkyl halides. Two selected applications of N-heterocycle-boryl radicals are also proposed herein, for radical polymerization and for radical dehalogenation reactions.
- Tehfe, Mohamad-Ali,Schweizer, Stephane,Chany, Anne-Caroline,Ysacco, Cedric,Clement, Jean-Louis,Gigmes, Didier,Morlet-Savary, Fabrice,Fouassier, Jean-Pierre,Neuburger, Markus,Tschamber, Theophile,Blanchard, Nicolas,Lalevee, Jacques
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supporting information
p. 5054 - 5063
(2014/05/06)
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- Facile esterification of alcohols with 2-Acyl-4,5-dichloropyridazin-3(2 H)-ones under Friedel-Crafts conditions
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This paper describes the esterification of aromatic and aliphatic alcohols by using 2-acyl-4,5-dichloropyridazin-3(2H)-ones as an acyl source under Friedel-Crafts conditions. Twelve alcohols were reacted with four 2-acyl-4,5-dichloropyridazin-3(2H)-ones in the presence of AlCl3 in tetrahydrofuran at room temperature to give the corresponding esters in moderate to excellent yields. Thus, 2-acylpyridazin-3(2H)-ones serve as good and atom-economic acyl sources for the esterification of aromatic alcohols under Friedel-Crafts conditions, representing a rapid, practical, and efficient method of esterification. Georg Thieme Verlag Stuttgart. New York.
- Kim, Bo Ram,Sung, Gi Hyeon,Ryu, Ki Eun,Yoon, Hyo Jae,Lee, Sang-Gyeong,Yoon, Yong-Jin
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p. 1909 - 1915
(2014/08/18)
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- In situ generated acylimidazolium acetate as an efficient catalyst and acylating agent for the acetylation of alcohols, phenols, and amines at ambient temperature
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Acylimidazolium acetate was readily prepared in situ from the reaction of imidazole with acetic anhydride and subsequently acted as a catalyst and acylating agent for the efficient acetylation of alcohols, phenols, and amines at ambient temperature.
- Nowrouzi, Najmeh,Alizadeh, Seyedeh Zahra
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p. 1787 - 1790
(2013/10/21)
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- A new ferrocene-based bulky pyridine as an efficient reusable homogeneous catalyst
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An effective approach to reusing a homogeneous catalyst has been demonstrated. A ferrocene-based bulky pyridine has been synthesized and utilized as a homogeneous catalyst for the synthesis of benzoylfumarates as well as for acetylation. After the reaction, the catalyst was separated by simple precipitation and reused without appreciable loss of activity. The Royal Society of Chemistry 2013.
- Kashyap, Bishwapran,Phukan, Prodeep
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p. 15327 - 15336
(2013/09/02)
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- Intramolecular vinyl quinone Diels-Alder reactions: Asymmetric entry to the cordiachrome core and synthesis of (-)-isoglaziovianol
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A short and asymmetric entry to the core structure of the cordiachromes has been developed, allowing access to (-)-isoglaziovianol in seven steps. Our synthesis includes a Trost asymmetric allylic alkylation and a reaction cascade triggered by a vinyl quinone Diels-Alder reaction and followed by intramolecular nucleophilic interception.
- Loebermann, Florian,Weisheit, Lara,Trauner, Dirk
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supporting information
p. 4324 - 4326
(2013/09/24)
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- Steric control of site selectivity in the Pd-catalyzed C-H acetoxylation of simple arenes
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This report describes the use of an oxidant and a ligand to control site selectivity in the Pd(OAc)2-catalyzed C-H acetoxylation of simple arenes. The use of MesI(OAc)2 as the terminal oxidant in combination with acridine as the ligand results in primarily sterically controlled selectivity. In contrast, with Pd(OAc)2 as the catalyst and PhI(OAc)2 as the oxidant, electronic effects dominate the selectivity of arene C-H acetoxylation.
- Cook, Amanda K.,Emmert, Marion H.,Sanford, Melanie S.
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supporting information
p. 5428 - 5431
(2013/11/19)
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- Palladium-catalyzed acetoxylation of arenes by novel sulfinyl n-heterocyclic carbene ligand complexes
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A series of novel ligands based on N-heterocyclic carbene and sulfoxide functionalities have been prepared and characterized. Pd(II) complexes have been synthesized by transmetalation from the corresponding NHC-Ag derivatives, and their behavior as catalysts has been studied in arene C-H bond oxidative activation. Studies conducted toward the elucidation of the reaction mechanism of the acetoxylation suggest a C-H activation step at Pd(IV) rather than Pd(II) intermediates.
- Tato, Francisco,Garcia-Dominguez, Andres,Cardenas, Diego J.
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supporting information
p. 7487 - 7494
(2014/04/03)
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- Catalyst-free esterification of alcohols using 2-acyl-4,5- dichloropyridazinones under microwave conditions
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Efficient and green esterification is of great importance. In this work, we demonstrate the catalyst-free esterification of alcohols by their reaction with 2-acyl-4,5-dichloropyridazin-3(2H)-ones under microwave irradiation. Aliphatic and aromatic alcohols were converted into the corresponding esters in good to excellent yields under microwave irradiation in solvent or solvent-free conditions. It is noteworthy that the reaction is catalyst-free, atom-economic, and rapid and that the process is inexpensive.
- Kim, Bo Ram,Sung, Gi Hyeon,Lee, Sang-Gyeong,Yoon, Yong Jin
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supporting information
p. 3234 - 3237
(2013/04/24)
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- Rapid and Ecofriendly Esterification of Alcohols with 2-Acylpyridazinones
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Atom-economical esterification is of great importance in green chemistry. In this work, we demonstrated the catalyst and additive free esterification of alcohols by their reaction with 2-acyl-4,5-dichloropyridazin-3(2H)- ones without solvent at 100 oC. Aliphatic and aromatic alcohols were converted into the corresponding esters in good to excellent yields. It is noteworthy that the reaction is solvent-free, atom-economic, easy-workup, and rapid and that the process is inexpensive.
- Kim, Bo Ram,Sung, Gi Hyeon,Ryu, Ki Eun,Kim, Jeum-Jong,Yoon, Yong-Jin
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p. 3410 - 3414
(2014/01/06)
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- O-acylation of substituted phenols with various alkanoyl chlorides under phase-transfer catalyst conditions
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Esterification of several types of mono-and disubstituted phenols with various mono-and dialkanoyl chlorides was performed in phase-transfer catalysis conditions, using tetrabutylammonium chloride in a mixture of aqueous NaOH and dichloromethane. The process is particularly efficient (almost quantitative yields) as well as rapid (only 5 min reaction time, at a temperature of0°C). Taylor & Francis Group, LLC.
- Simion, Alina Marieta,Hashimoto, Iwao,Mitoma, Yoshiharu,Egashira, Naoyoshi,Simion, Cristian
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experimental part
p. 921 - 931
(2012/02/01)
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- Polyvinylpolypyrrolidone-bound boron trifluoride: A highly efficient catalyst for acylation of alcohols, phenols and trimethylsilyl ethers by acetic anhydride
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A highly efficient method for the acylation of alcohols, phenols and trimethylsilyl ethers with acetic anhydride is described using polyvinylpolypyrrolidone-bound boron trifluoride (PVPP-BF3) under mild and heterogeneous conditions at room temperature in good to excellent yields. The polyvinylpolypyrrolidone-boron trifluoride complex shows more water tolerant, non-corrosive and stable solid catalyst elevated Lewis acid properties.
- Mokhtary, Masoud,Qandalee, Mohammad,Najafizadeh, Faranak
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experimental part
p. 389 - 393
(2012/08/28)
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- 4-(N,N-dimethylamino)pyridine-embedded nanoporous conjugated polymer as a highly active heterogeneous organocatalyst
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We report herein for the first time the incorporation of a versatile organocatalyst, 4-(N,N-dimethylamino)pyridine (DMAP), into the network of a nanoporous conjugated polymer (NCP) by the "bottom-up" approach. The resulting DMAP-NCP material possesses highly concentrated and homogeneously distributed DMAP catalytic sites (2.02 mmol g-1). DMAP-NCP also exhibits enhanced stability and permanent porosity due to the strong covalent linkage and the rigidity of the "bottom-up" monomers. As a result, DMAP-NCP shows excellent catalytic activity in the acylation of alcohols with yields of 92-99 %. The DMAP-NCP catalyst could be easily recovered from the reaction mixture and reused in at least 14 consecutive cycles without measurable loss of activity. Moreover, the catalytic acylation reaction could be performed under neat and continuous-flow conditions for at least 536 h of continuous work with the same catalyst activity. Copyright
- Zhang, Yuan,Zhang, Yong,Sun, Ya Lei,Du, Xin,Shi, Jiao Yi,Wang, Wei,Wang, Wei David
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experimental part
p. 6328 - 6334
(2012/06/18)
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- Characterization of novel Cs and K substituted phosphotungstic acid modified MCM-41 catalyst and its catalytic activity towards acetylation of aromatic alcohols
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TheMCM-41 supported Cs2.5H0.5PW12O 40 and K2.5H0.5PW12O40 salts were synthesized by incipient wetness impregnation method. The solids were characterized by N2 adsorption-desorption isotherms, FTIR, XRD, and temperature programmed desorption, etc. This catalyst has been found to exhibit excellent activity for acetylation of phenolic compounds. The catalyst is stable and reusable giving 96% conversion with 100% selectivity towards acetate products. Indian Academy of Sciences.
- Rana, Surjyakanta,Mallick, Sujata,Rath, Dharitri,Parida
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p. 1117 - 1125
(2013/03/13)
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- Borated zirconia modified with ammonium metatungstate as catalyst in alcohol acetylation
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Samples of tungsten-modified borated zirconia were prepared to be used as catalyst in 2-phenoxyethanol acetylation. The borated zirconias were obtained by impregnation of two zirconias (S2 and S4) obtained by the micellar method using different zirconium precursor concentrations with boric acid solution containing 0.3 moles B/dm3. These solids and the parent zirconias were impregnated with two concentration levels of ammonium metatungstate solutions (0.11 and 0.22 moles W/dm3). The solids containing boron mainly have amorphous characteristics and strong acidity, while those that contain only tungsten showed stronger acidity and evidence of the presence of a crystalline phase. The specific surface area and the pore volume slightly decreased in the solids obtained by adding tungsten to borated zirconia, and more markedly in those that contain only tungsten, and the mean pore size increased with respect to the parent support. It was observed that in the 2-phenoxyethanol acetylation using acetic acid as acylating agent and tungsten-modified borated zirconia as catalyst, the yield to acetylated product was high and it is correlated with the acid strength of the catalysts. In turn, the solids that contain only tungsten have a correlation with the acidity, but lead to low yield values due to a poorer dispersion of the tungsten species. The best yield was obtained with the catalyst prepared with the borated S4 zirconia containing 15% g B2O3/100 g support and 12.5% g W/100 g support. Using this catalyst and the same reaction conditions, the acetylation of different alcohols and phenols was studied, the reactivity order being as follows: primary alcohols > secondary alcohols > phenols.
- Osiglio, Lilian,Sathicq, ángel G.,Romanelli, Gustavo P.,Blanco, Mirta N.
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experimental part
p. 97 - 103
(2012/07/14)
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- Iron-doped single-walled carbon nanotubes as new heterogeneous and highly efficient catalyst for acylation of alcohols, phenols, carboxylic acids and amines under solvent-free conditions
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Iron-doped single-walled carbon nanotubes (Fe/SWCNTs) represent an efficient and new heterogeneous reusable catalyst for the acylation of a variety of alcohols, phenols, carboxylic acids and amines with acid chlorides or acid anhydrides under solvent-free conditions. The reactions of various primary, secondary, tertiary, and benzylic alcohols, diols, phenols, as well as aromatic and aliphatic amines give acylated adducts in good to excellent yields.
- Sharghi, Hashem,Jokar, Mahboubeh,Doroodmand, Mohammad Mahdi
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experimental part
p. 426 - 442
(2011/04/15)
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- Comparisons of O-acylation and Friedel-Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: Effective synthesis of optically active homotyrosines
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Reactions involving phenol derivatives and acyl chlorides have to be controlled for competitive O-acylations and C-acylations (Friedel-Crafts acylations and Fries rearrangements) in acidic condition. The extent for these reactions in trifluoromethanesulfonic acid (TfOH), which is used as catalyst and solvent, is examined. Although diluted TfOH was needed for effective O-acylation, concentrated TfOH was required for effective C-acylations in mild condition. These results have been applied to the novel synthesis of homotyrosine derivatives. Both Fries rearrangement of N-TFA-Asp(OBn)-OMe and Friedel-Crafts acylation of phenol with N-TFA-Asp(Cl)-OMe in TfOH afforded the homotyrosine skeleton, followed by reduction and deprotection afforded homotyrosines maintaining stereochemistry of Asp as an optically pure form.
- Murashige, Ryo,Hayashi, Yuka,Ohmori, Syo,Torii, Ayuko,Aizu, Yoko,Muto, Yasuyuki,Murai, Yuta,Oda, Yuji,Hashimoto, Makoto
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experimental part
p. 641 - 649
(2011/03/19)
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- Silver triflate catalyzed acetylation of alcohols, thiols, phenols, and amines
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A variety of alcohols, thiols, phenols, and amines were subjected to acetylation reaction using acetic anhydride in the presence of catalytic quantity of silver triflate. The method described has a wide range of applications, proceeds under mild conditions, does not involve cumbersome workup, and the resulting products are obtained in high yields within a reasonable time. Georg Thieme Verlag Stuttgart · New York.
- Das, Rima,Chakraborty, Debashis
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experimental part
p. 1621 - 1625
(2011/06/25)
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- Highly efficient and versatile acetylation of alcohols, phenols and amines catalyzed by methylenediphosphonic acid (MDP) under solvent-free conditions
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Methylenediphosphonic Acid (MDP) was found to be a simple, cheap and reusable heterogeneous catalyst for the acetylation of structurally diverse alcohols, phenols and amines with acetic anhydride under solvent-free conditions at room temperature. This method showed preferential selectivity for the acetylation of the amino group in the presence of hydroxyl group. The method is very mild and the yields were in excellent.
- Xie, Minhao,Wang, Hongyong,Wu, Jun,He, Yongjun,Liu, Yaling,Zou, Pei
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experimental part
p. 884 - 886
(2012/04/23)
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- Gold(III)-catalyzed direct acetoxylation of arenes with iodobenzene diacetate
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AuCl3-catalyzed direct acetoxylation of electron-rich aromatic compounds has been achieved with iodobenzene diacetate as the acetoxylation reagent.
- Qiu, Di,Zheng, Zhitong,Mo, Fanyang,Xiao, Qing,Tian, Yu,Zhang, Yan,Wang, Jianbo
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supporting information; experimental part
p. 4988 - 4991
(2011/11/13)
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