- Octacarbonyl dicobalt-catalyzed selective transformation of ethyl diazoacetate into organic products containing the ethoxycarbonyl carbene building block
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In the presence of 1 mol% octacarbonyl dicobalt ethyl diazoacetate can be transformed at room temperature and carbon monoxide pressure selectively into diethyl 2-diazo-3-oxo-pentanedicarboxylate or in the presence of an alcohol (methanol, ethanol, tert-bu
- Tuba, Robert,Ungváry, Ferenc
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- Indium as a reducing agent. Chemoselective reduction of α-halocarbonyl compounds and benzyl halides by indium metal in water under sonication
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Indium metal in water reduces a-halocarbonyl compounds and benzyl iodides to the corresponding dehalogenated products in excellent yields under sonication although simple alkyl and aryl iodides remained inert under these conditions.
- Ranu, Brindaban C.,Dutta, Pinak,Sarkar, Arunkanti
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- An unusual synthesis of malonates
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The reaction of palladium diacetate, triethylamine, ethyl chlorocarbonate and carbon monoxide in acetonitrile at room temperature gives a good yield of diethyl malonate. By 13C labelling of each of the reagents in turn it has been proven that the methylene group of the malonate comes from an acetate originally bonded to PdII.
- Barton, Derek H. R.,Langlois, Pascal,Okano, Takashi,Ozbalik, Nubar
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- Mechanism of the cobalt-catalyzed carbonylation of ethyl diazoacetate
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Carbonyl cobalt complexes serve as catalysts or catalyst precursors for the facile and selective transformation of primary diazoalkanes into the corresponding ketene. The mechanism of this carbonylation reaction has been elucidated in the case of ethyl diazoacetate as model diazoalkane using octacarbonyl dicobalt as the catalyst precursor. Dinuclear cobalt complexes having ethoxycarbonylcarbene ligand(s) in bridging position(s) have been identified as active intermediary of the catalytic cycles and their relevant chemical properties have been explored. Key step of the carbonylation is the formation of the highly reactive ethoxycarbonylketene by intramolecular coupling of a carbonyl ligand with the ethoxycarbonylcarbene ligand. DFT calculations reveal that the ketene formation takes place via a rapid coupling of the carbene ligand with one terminal CO followed by coordination of an external carbon monoxide and by a facile intramolecular rearrangement and ketene elimination. The ethoxycarbonylketene can be in situ trapped by OH, NH, or CH acid compounds or by N-substituted imines. In the presence of ethanol diethyl malonate is the only product of the catalytic carbonylation of ethyl diazoacetate. On the bases of the kinetics of the composing steps of the catalytic cycles, localization of the rate-determining step(s) under various reaction conditions has been made.
- Ungvári, Neszta,F?rdos, Eszter,Kégl, Tamás,Ungváry, Ferenc
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- Zinc- and indium-promoted conjugate addition-cyclization reactions of ethenetricarboxylates with propargylamines and alcohol: Novel methylenepyrrolidine and methylenetetrahydrofuran syntheses
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A new zinc- and indium-promoted conjugate addition-cyclization reaction to afford nitrogen- and oxygen-containing five-membered heterocycles has been developed. Reaction of ethenetricarboxylates with propargylamines (1 equiv) in the presence of ZnBr2 or InBr3 afforded methylenepyrrolidines in high yields. The stoichiometric use of ZnBr2 or InBr3 at room temperature and the catalytic use of InBr 3-Et3N at 80°C were effective. Reaction of ethenetricarboxylates with propargyl alcohol in the presence of ZnBr2 or InBr3 afforded methylenetetrahydrofurans.
- Morikawa, Satoshi,Yamazaki, Shoko,Furusaki, Yoshiteru,Amano, Naoya,Zenke, Kazumi,Kakiuchi, Kiyomi
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- Synthesis of monoesters and diesters using eco-friendly solid acid catalysts - Cerium(IV) and thorium(IV) phosphates
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In the present endeavour, amorphous cerium phosphate (CP) and thorium phosphate (TP) have been synthesized by sol-gel method and also under microwave irradiation to yield CPM and TPM. CP, TP, CPM and TPM have been characterized for elemental analysis (ICP-AES), spectral analysis (FTIR), thermal analysis (TGA), X-ray diffraction studies, SEM, EDX, surface area (BET) and surface acidity (NH3-TPD). The potential use of these materials as solid acid catalysts has been explored by studying esterification as a model reaction. Monoesters such as ethyl acetate (EA), propyl acetate (PA), butyl acetate (BA), benzyl acetate (BzAc) and diesters such as diethyl malonate (DEM), diethyl succinate (DES), dibutyl phthalate (DBP), dioctyl phthalate (DOP) have been synthesized. Esterification conditions have been optimized by varying several parameters such as reaction time, catalyst amount and mole ratio of reagents. The catalytic activity has been compared and correlated with reference to surface acidity of the catalysts. It is found that catalytic activity of CPM > CP > TP M > TP. The regenerated catalysts could be reused upto two catalytic runs without significant loss in % yields of esters formed. The highlighting feature of the present work is the catalysts CPM and TPM that are synthesized in a much shorter reaction time with higher surface acidity giving good % yield of esters.
- Parangi, Tarun,Wani, Bina,Chudasama, Uma
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- The synthesis of polymeric catalyst using ion exchange resin and its application for esterification
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The copolymer complexes have been synthesized from cation and/or anion resin with metal catalyst such as aluminum chloride or iron(III) chloride. Electron microprobe X-ray analysis demonstrated that aluminum and iron were distributed uniformly in the copolymer complex. The catalytic activity for esterification of dibasic organic acids was discussed and showed that copolymer complex from porous type cation exchange resin was much better catalyst than that from gel type. Copolymer complexes have been synthesized from cation and/or anion resin with metal catalyst such as aluminum chloride or iron (III) chloride. Electron microprobe X-ray analysis demonstrated that aluminum and iron were distributed uniformly in the copolymer complex. The catalytic activity for esterification of dibasic organic acids was discussed and showed that copolymer complex from the porous type cation exchange resin was a much better catalyst than that from the gel type.
- Whang,Lee,Lee
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- Design, Synthesis, and Dual Evaluation of Quinoline and Quinolinium Iodide Salt Derivatives as Potential Anticancer and Antibacterial Agents
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A series of novel quinoline and quinolinium iodide derivatives were designed and synthesized to discover potential anticancer and antibacterial agents. With regard to anticancer properties, in vitro cytotoxicities against three human cancer cell lines (A-549, HeLa and SGC-7901) were evaluated. The antibacterial properties against two strains, Escherichia coli (ATCC 29213) and Staphylococcus aureus (ATCC 8739), along with minimum inhibitory concentration (MIC) values were evaluated. The target alkyliodine substituted compounds exhibited significant antitumor and antibacterial activity, of which compound 8-((4-(benzyloxy)phenyl)amino)-7-(ethoxycarbonyl)-5-propyl-[1,3]dioxolo[4,5-g]quinolin-5-ium (12) was found to be the most potent derivative with IC50 values of 4.45±0.88, 4.74±0.42, 14.54±1.96, and 32.12±3.66 against A-549, HeLa, SGC-7901, and L-02 cells, respectively, stronger than the positive controls 5-FU and MTX. Furthermore, compound 12 had the most potent bacterial inhibitory activity. The MIC of this compound against both E. coli and S. aureus was 3.125 nmol ? mL?1, which was smaller than that against the reference agents amoxicillin and ciprofloxacin.
- Jin, Guofan,Li, Zhenwang,Qi, Xueyong,Sun, Xianyu,Xiao, Fuyan,Zhao, Lei
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- Co2(CO)8-induced domino reactions of ethyl diazoacetate, carbon monoxide and ferrocenylimines leading to 2-(1-ferrocenyl-methylidene)-malonic acid derivatives
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Novel 2-(1-ferrocenyl-methylidene)-malonic acid derivatives are obtained upon reacting ethyl diazoacetate, carbon monoxide and ferrocenylimines in the presence of Co2(CO)8 as catalyst under mild conditions. Presumably, the reaction involves three steps taking place in a domino fashion, (i) carbonylation of ethyl diazoacetate leading to a ketene derivative, (ii) [2+2] cycloaddition of the ketene with the ferrocenylimine present in the reaction mixture resulting in the formation of a β-lactam and (iii) N(1)-C(4) cleavage of the β-lactam ring. In most cases, 2-(1-ferrocenyl-methylidene)-malonic acid derivatives are obtained as a separable mixture of E- and Z-isomers in ratios depending on the structure of the imine component.
- Balogh, János,Kégl, Tamás,Ungváry, Ferenc,Skoda-F?ldes, Rita
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- Rhodium-catalyzed double carbonylation of diiodomethane in the presence of triethylorthoformate
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Catalytic double carbonylation of diiodomethane in triethylorthoformate in the presence of a homogeneous rhodium complex gives diethylmalonate in a fairly good yield.
- Cheong, Minserk,Kim, Mi-Na,Shim, Ji Yeon
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- A CONVENIENT METHOD FOR ENZYMATIC BENZYL-ALKYL TRANSESTERIFICATION UNDER MILD NEUTRAL CONDITIONS
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Lipases from Candida cylindracea and from Pseudomonas fluorescens efficiently catalyse the benzyl to alkyl transesterification in organic solvents under mild conditions in nearly quantitative yields.
- Gutman, Arie L.,Shkolnik, Eleonora,Shapira, Michal
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- An efficient renewable-derived surfactant for aqueous esterification reactions
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An efficient and simple approach for the aqueous esterification of a range of carboxylic acids with alcohols has been developed using catalytic amounts of a glucose-derived N-alkanoyl-N-methyl-1-glycamine non-ionic biosurfactant (C12MG). Excellent yields to final products were obtained under mild conditions and the protocol was amenable to both aromatic and long alkyl chain acids (e.g. fatty acids).
- Rajabi, Fatemeh,Luque, Rafael
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- Vapor pressures and enthalpies of vaporization of a series of the symmetric linear n -alkyl esters of dicarboxylic acids
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Vapor pressures and the molar enthalpies of vaporization of the linear aliphatic alkyl esters of dicarboxylic acids R-CO2-(CH 2)n-CO2-R with n = (0 to 4) with R = C 2H5, n-C3H7, and n-C 4H9 have been determined using the transpiration method. A linear correlation of enthalpies of vaporization (at T = 298.15 K) of the esters with the number n and with Kovat's indices has been found, proving the internal consistency of measured data.
- Lipp, Svetlana V.,Krasnykh, Eugenii L.,Verevkin, Sergey P.
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- Synthesis of coumarin-3-carboxylic esters via FeCl3-catalyzed multicomponent reaction of salicylaldehydes, Meldrum's acid and alcohols
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A FeCl3-catalyzed multicomponent reaction was developed for the facile synthesis of coumarin-3-carboxylic ester derivatives in a highly atom-economic and environmentally friendly way. Using simple and cheaply available salicylaldehydes, Meldrum's acid and alcohols as the starting materials, the method needs no extra additives and features wide substrate scope, good functional group tolerance and mild reaction conditions.
- He, Xinwei,Shang, Yongjia,Zhou, Yao,Yu, Zhiyu,Han, Guang,Jin, Wenjing,Chen, Jiaojiao
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- A Mild, Simple, and Convenient Synthesis of Diesters from Malonyl or Succinyl Dichloride and Alcohols Catalyzed by Potassium Tetracarbonylhydridoferrate, KHFe(CO)4, as a New Catalyst
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A large variety of alcohols react with acyl halides of dicarboxylic acids such as malonyl dichloride and succinyl dichloride in the presence of a catalytic amount of tetracarbonylhydridoferrate at room temperature under carbon monoxide or nitrogen to give the corresponding diesters in good yields.
- Shim, Sang Chul,Huh, Keun Tae,Park, Woo Hyun
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- Sequential fullerenylation of bis-malonates-efficient access to oligoclusters with different fullerene building blocks
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A method for the sequential fullerenylation of bis-malonates with parent C60 and C2v-symmetric pentakis-adducts is reported. This approach relies on the finding that (a) chloromalonates can be used for the nucleophilic cyclopropanation of [6,6] double bonds of C60, and (b) chloromalonates, in contrast to bromomalonates, do not undergo base-catalyzed halogen exchange reactions. For the proof of concept, we synthesized a heptafullerene by using a divergent approach based on a fullerene hexakis-adduct with six bis-malonate addends in octahedral positions, each of which is suitable for an additional cyclopropanation of a fullerene building block. A sequence for the selective fullerenylation of bis-malonates with C60 and its exohedral C2v-symmetric pentakis-adducts has been developed. This method enables the straightforward synthesis of highly functional fullerene derivatives such as the heptafullerene 1.
- Wasserthal, Lennard K.,Kratzer, Andreas,Hirsch, Andreas
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- Carbazolic porous organic framework as an efficient, metal-free visible-light photocatalyst for organic synthesis
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We report the visible-light-promoted photocatalytic activity of a highly porous carbazolic organic framework, Cz-POF-1, toward three prototypic organic transformations: net reductive dehalogenation of phenacyl bromide and its derivatives, net oxidative hydroxylation of arylboronic acids, and redox-neutral α-alkylation of aldehydes. We show that the extended π-conjugation in Cz-POF-1 enhances its visible light absorption, and the large porosity accelerates the reaction rate. For α-alkylation of aldehydes, Cz-POF-1 requires less strict reaction conditions and can be easily recovered and reused for up to 10 times. This work reveals a bright future for Cz-POFs as a new generation of metal-free photocatalysts for organic synthesis.
- Luo, Jian,Zhang, Xiang,Zhang, Jian
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- Fe2(SO4)3 · xH2O catalytic esterification of aliphatic carboxylic acids with alcohols
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Treatment of various alcohols with aliphatic carboxylic acids in the presence of a catalytic amount of Fe2(SO4)3 · xH2O to give the corresponding esters in good yields.
- Zhang, Gui-Sheng
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- Kinetics of ionisation of carbon acids in non-aqueous media: detritiation of diethyl malonate by heterocyclic bases
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To investigate proton transfer processes in non-aqueous media, two procedures have been developed of general applicability for the measurement of detritiation rates of carbon acids.One method is a variation of an existing solvent extraction procedure but with inclusion of a trace of trifluoroacetic acid, while the other involves the simple modification of a gas chromatograph so as to function as a radio-gas chromatograph.They have been established by studying the detritiation of diethyl malonate in six different solvents (dimethylformamide, dimethyl sulfoxide, sulfolane, hexamethylphosphortriamide, tetrahydrofuran, ethanol) as catalyzed by various heterocyclic bases (substituted pyridines, imidazoles, benzimidazoles, pyrrole, pyrazole, purine, adenosine).The results are discussed in terms of solvation effects and catalyst structure.An approximate Broensted correlation is found to exist between log kTB for detritiation determined in DMSO and the pKa of the conjugate base measured in water at 25 deg C.
- Davey, John P.,Jones, John R.,Buncel, Erwin
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- Synthesis of 3-substituted and 3,4-disubstituted pyrazolin-5-ones
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The synthesis of 3-substituted and 3,4-disubstituted pyrazolin-5-ones from acylated ethyl acetoacetates and diethyl malonates is described. The reaction of acylated ethyl acetoacetates and diethyl acetylmalonate with hydrazine (98%) gave 3-substituted pyrazolin-5-ones and malonyldihydrazide, respectively, following a deacetylation-condensation sequence. The reaction of ethyl 2-acetyl-3-hydroxy-2-butenoate and diethyl 2-(1-hydroxyethylidene)malonate with hydrazine monohydrochloride yielded ethyl 3,5-dimethyl-1H-pyrazole-4-carboxylate and 4-ethoxycarbonyl-3-methylpyrazolin-5-one, respectively, following a dehydration-cyclocondensation sequence, in high yields.
- Jung, Jae-Chul,Watkins, E.Blake,Avery, Mitchell A
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- Modelling intermediates in the catalytic carbonylation of CH2I2 to malonate esters; Evidence for a ketene pathway
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From model intermediates and from labelling studies, a ketene-based mechanism is proposed for the double carbonylation of CH2I2 to malonate esters catalysed by [RhX(CO)(PEt3)2] and for the deactivation of the catalyst.
- Weston, William S.,Lightfoot, Philip,Cole-Hamilton, David J.
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- On the scope of radical reactions in aqueous media utilizing quaternary ammonium salts of phosphinic acids as chiral and achiral hydrogen donors
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A broad range of fundamental free radical reactions such as hydrogen atom transfer, radical deoxygenations, and radical cyclizations utilizing quaternary ammonium salts of phosphinic acids as chiral and achiral hydrogen donors at room temperature are investigated. The reactions proceed in good to excellent yields with some degree of enantioselectivity.
- Perchyonok,Tuck, Kellie L.,Langford, Steven J.,Hearn, Milton W.
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- Promoting charge separation in donor-acceptor conjugated microporous polymers: Via cyanation for the photocatalytic reductive dehalogenation of chlorides
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Conjugated microporous polymers (CMPs) have emerged as promising heterogeneous photocatalysts for organic transformations owing to their structural designability and functional versatility. However, limited by the insufficient separation of the photo-generated excitons, their photocatalytic efficiency falls far short of expectations. Herein, we demonstrate a cyanation strategy to promote charge carrier separation in CMPs by selectively incorporating carbazole and cyano groups as electron-donating and electron-withdrawing units, respectively. The resulting CMPs feature π-extended donor (D)-acceptor (A) conjugation structures endowing them with distinct semiconducting properties, in which the efficient charge separation and transfer and wide visible-light absorption are facilitated. Compared to the cyano-free counterpart, the cyano-functionalized CMPs showed superior photocatalytic efficiency as exemplified by photocatalytic reductive dehalogenation of chlorides. More prominently, full recyclability of the designed CMPs as well as catalytic activity for at least ten runs without the loss of catalytic performance in photocatalytic reductive dehalogenation of chlorides demonstrated their robustness and sustainability. This journal is
- Deng, Jiyong,Fang, Zhengjun,Lan, Donghui,Liao, Yunfeng,Liu, Qingquan,Zhang, Weijie,Zhou, Xiang
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p. 7151 - 7159
(2021/11/17)
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- One-pot production of diethyl maleate via catalytic conversion of raw lignocellulosic biomass
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The conversion of lignocellulose into a value-added chemical with high selectivity is of great significance but is a big challenge due to the structural diversities of biomass components. Here, we have reported an efficient approach for the one-step conversion of raw lignocellulose into diethyl maleate by the polyoxometalate ionic liquid [BSmim]CuPW12O40 in ethanol under mild conditions. The results reveal that all of the fractions in biomass, i.e., cellulose, lignin and hemicellulose, were simultaneously converted into diethyl maleate (DEM), achieving a 329.6 mg g-1 yield and 70.3% selectivity from corn stalk. Importantly, the performance of the ionic liquid catalyst [BSmim]CuPW12O40 was nearly twice that of CuHPW12O40, which can be attributed to the lower incorporation of the Cu2+ site in [BSmim]CuPW12O40. Hence, this process opens a promising route for producing bio-based bulk chemicals from raw lignocellulose without any pretreatment.
- Cai, Zhenping,Chen, Rujia,Jiang, Lilong,Li, Fukun,Li, Xuehui,Long, Jinxing,Zhang, Hao
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supporting information
p. 10116 - 10122
(2021/12/24)
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- Green pepper flavor compound, preparation method thereof, food additive and green pepper flavor food
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The invention relates to a green pepper flavor compound, a preparation method thereof, a food additive and a green pepper flavor food. The green pepper flavor compound has the following structural formula, the green pepper flavor compound is a leaf alcohol ester compound, different from strong fresh grass leaf fragrance of leaf alcohol and grease gas of a traditional long-chain leaf alcohol estercompound, the green pepper flavor compound has obvious green pepper flavor different from leaf alcohol and obvious fragrance, and a new thought is provided for development of the leaf alcohol ester compound.
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Paragraph 0058-0062; 0076-0080; 0088-0092
(2020/07/21)
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- Apple flavor compound, preparation method thereof and food additive
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The invention relates to an apple flavor compound, a preparation method thereof and a food additive. The apple flavor compound has a structural formula shown as the specification, the apple flavor compound can be named as 1-(1-(1-(3, 3-dimethylcyclohexyl)ethyl)3-ethyl malonic acid malonate. Experiments prove that the compound has obvious mature sweet apple fragrance, can be used in food additiveswith apple fragrance, and provides a new source for the apple flavor compound.
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Paragraph 0059-0063; 0077-0080; 0086-0089
(2020/07/13)
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- Visible-light-induced photocatalyst-free C-3 functionalization of indoles with diethyl bromomalonate
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A visible-light induced green and efficient method is developed for the synthesis of α-indolyl diethyl malonates. The reaction proceeds without any photocatalysts or ligands in a green solvent in a short time. Moreover, the reaction mechanism has been clearly studied by control experiments, spectrophotometric studies and density functional theory (DFT) calculations. The results showed that the photocatalyst-free transformation may proceed via an XB-promoted radical process. The EDA complex formation of diethyl bromomalonate with a base is the main reason for the reaction initiation.
- Gu, Guangmiao,Huang, Mengmeng,Kim, Jung Keun,Li, Yabo,Wu, Yangjie,Zhang, Jianye
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supporting information
p. 2543 - 2548
(2020/05/13)
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- Electrochemical Alkoxyhalogenation of Alkenes with Organohalides as the Halide Sources via Dehalogenation
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A general, ideal atom utilization electrochemical technology to enable alkene alkoxyhalogenation and organohalide dehalogenation in one pot is presented. This technology is highlighted by convergent strategy integrating several reactions, such as alkene alkoxyhalogenation, organohalide dehalogenation, and dehalogenation deuteration. Experimental data suggest that alkenes have the lowest oxidation potential, which lead to anodic conversion of the C═C bond to the radical cation intermediates, and cathodic transformations of organohalides, including alkyl and aryl halides, as the nucleophilic halogen sources.
- Li, Jin-Heng,Li, Yang,Luo, Mu-Jia,Song, Ren-Jie,Zhang, Ting-Ting
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supporting information
p. 7250 - 7254
(2020/10/05)
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- PREPARATION OF DEOXYCHOLIC ACID
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The present invention relates to new and improved processes for the preparation of deoxycholic acid (DCA) and pharmaceutically acceptable salts thereof, as well as to DCA and pharmaceutically acceptable salts thereof, the carbon atoms of which are derived partially or solely from plant sources.
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Page/Page column 92; 93
(2019/05/15)
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- Reducing dehalogenating method of organic halogenated compound
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The invention discloses a reducing dehalogenating method of an organic halogenated compound. The reducing dehalogenating method comprises: mixing an organic halogenated compound R-X, a non-noble metalpromoter, a sulfide and an alkali, and carrying out a reducing dehalogenating reaction to obtain a reducing product R-H, wherein R is at least one selected from alkyl and aryl, and X is at least oneselected from iodine, bromine and chlorine. According to the present invention, the types and the ratio (especially the specific type of the promoter) of various raw materials used in the reducing dehalogenating reaction, the corresponding reaction conditions and the like are researched and improved, such that the problems of use of highly-toxic or expensive reagent, poor tolerance of the group, narrow application range of the substrate and the like in the prior art can be effectively solved.
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Paragraph 0099; 0100; 0102; 0124; 0129; 0130
(2019/02/10)
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- Size-selective mesoporous silica-based Pt(II)complex as efficient and reusable photocatalytic material
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The grafting of a Pt(II)photocatalyst into three different mesoporous silica-based materials with different particle sizes and pore sizes was easily achieved through an amide bond formation. The analysis and results of the different characterization techniques showed that the catalyst is immobilized inside the pores of the materials and the photophysical properties of the catalyst are preserved after the covalent anchoring. The photocatalytic material catalyzed efficiently the debromination reaction of different substrates and is reused without detriment in its catalytic activity. In addition, the incorporation of the catalyst into mesoporous silica materials with different pore size allows the selective debromination of substrates by size discrimination.
- González-Mu?oz, Daniel,Casado-Sánchez, Antonio,del Hierro, Isabel,Gómez-Ruiz, Santiago,Cabrera, Silvia,Alemán, José
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p. 374 - 383
(2019/05/01)
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- 8-Mercaptoquinoline as a Ligand for Enhancing the Photocatalytic Activity of Pt(II) Coordination Complexes: Reactions and Mechanistic Insights
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A family of quinoline-platinum(II) complexes as efficient photocatalysts is presented. Their key characteristic is their easy preparation by coordination of the readily available 8-hydroxy- or 8-thio-quinoline ligands, which are well known for their strong chelating ability to different metal ions. In the different photochemical transformations investigated, such as cross-dehydrogenative coupling, oxidation of arylboronic acids, and asymmetric alkylation of aldehydes, 8-mercaptoquinoline-Pt(II) complex proved to be the most general catalyst. Moreover, quenching experiments showed that, contrary to related methods reported in the literature, these complexes followed an oxidative quenching mechanism in all transformations studied. Besides, simulations performed with high-level ab initio methods of the complexes have helped to understand their photocatalytic activity.
- Casado-Sánchez, Antonio,Uygur, Mustafa,González-Mu?oz, Daniel,Aguilar-Galindo, Fernando,Nova-Fernández, José Luis,Arranz-Plaza, Judith,Díaz-Tendero, Sergio,Cabrera, Silvia,Manche?o, Olga García,Alemán, José
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p. 6437 - 6447
(2019/05/24)
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- Preparation method of malonic ester
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The invention provides a preparation method of malonic ester. Malonic ester is obtained by using 70-80 wt% of cyanoacetic acid, hydrogen chloride-alcoholic solution and corresponding alcohol as raw materials, and is subjected to the process of esterification, dealcoholic water, alcoholysis esterification, dealcoholization, neutralization and distillation. The preparation method chooses the cyanoacetic acid of reasonable concentration, reduces the heat-sensitive reaction of distillation dehydration when obtaining high concentration cyanoacetic acid, and reduces the difficulty of dehydration ofthe cyanoacetic acid raw materials; the method is high in operability, reasonable and economy, reduces the discharge of three wastes greatly, and has good social benefit.
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Paragraph 0046-0057
(2018/04/01)
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- Customizing Photoredox Properties of PXX-based Dyes through Energy Level Rigid Shifts of Frontier Molecular Orbitals
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Here we describe the synthesis of electron-rich PXX derivatives in which the energy levels of the excited states have been rigidly shifted through the insertion of imide groups. This has allowed the development of a new series of oxygen-doped photoredox-active chromophores with improved oxidizing and reducing properties. Capitalizing on the dehalogenation of organic halides as a model reaction, we could investigate the photooxidative and photoreductive potential of these molecules in model chemical transformations. Depending on the substrate, solvent and dye the reaction mechanism can follow different paths. This prompted us to consider the first chemoselective transformation protocol, in which two different C?Br bonds could be chemoselectively reacted through the sequential photoactivation of two different colorants.
- Sciutto, Andrea,Fermi, Andrea,Folli, Andrea,Battisti, Tommaso,Beames, Joseph M.,Murphy, Damien M.,Bonifazi, Davide
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supporting information
p. 4382 - 4389
(2018/03/05)
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- Synthetic method of malonate compound
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The invention discloses a synthetic method of a malonate compound. The method comprises the following steps: taking 3-halogenated propargyl compound as shown in a formula 1, alcohol as shown in a formula 2 and water as raw materials; placing the raw materials in an air atmosphere and at the room temperature to react under the conditions of a palladium catalyst and alkali to prepare the malonate compound as shown in a formula 3.
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Paragraph 0048-0050
(2018/05/16)
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- DBU-Based Dicationic Ionic Liquids Promoted Esterification Reaction of Carboxylic Acid with Primary Chloroalkane Under Mild Conditions
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Abstract: A series of DBU-based (DBU = 1, 8-diazabicyclo [5.4.0] undec-7-ene) dicationic ionic liquids with different anions were successfully synthesized by the reaction of DBU and 1, 6-dichlorohexane. Therein, the dicationic ionic liquid 1, 1′-(hexane-1, 6-diyl)bis(1, 8-diazabicyclo [5.4.0]undec-7-enium) dichlorine (IL-1) was successfully employed as an efficient catalyst in esterification reaction of carboxylic acids with primary chloroalkanes under mild conditions without any additional basic reagents. Moreover, the optimum catalyst could be efficiently reused for five times without any significant change on the catalytic effect. The improved protocol is not only efficient, but also green and pollution-free.
- Liu, Yang,Mao, Guijie,Zhao, Hongyan,Song, Jinyi,Han, Huatao,Li, Zhuofei,Chu, Wenyi,Sun, Zhizhong
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p. 2764 - 2771
(2017/09/14)
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- Selective Debromination and α-Hydroxylation of α-Bromo Ketones Using Hantzsch Esters as Photoreductants
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Two transformations initiated by photoinduced one-electron transfer to α-bromo ketones have been demonstrated. Hantzsch esters donate one electron to α-bromo ketones under photoirradiation, promoting reductive debromination. Subsequent reactions of the resulting radical species of the ketones with molecular oxygen and Hantzsch esters lead to α-hydroxylation or debromination, respectively. The relative dominance of the two pathways depends profoundly on the reaction conditions, including solvent, O2 levels, and the concentration of the Hantzsch esters. The synthetic protocols feature advantages because they require the environmentally benign sources, molecular oxygen and visible light.
- Jung, Jaehun,Kim, Jun,Park, Gyurim,You, Youngmin,Cho, Eun Jin
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- Structural Design Principle of Small-Molecule Organic Semiconductors for Metal-Free, Visible-Light-Promoted Photocatalysis
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Herein, we report on the structural design principle of small-molecule organic semiconductors as metal-free, pure organic and visible light-active photocatalysts. Two series of electron-donor and acceptor-type organic semiconductor molecules were synthesized to meet crucial requirements, such as 1) absorption range in the visible region, 2) sufficient photoredox potential, and 3) long lifetime of photogenerated excitons. The photocatalytic activity was demonstrated in the intermolecular C?H functionalization of electron-rich heteroaromates with malonate derivatives. A mechanistic study of the light-induced electron transport between the organic photocatalyst, substrate, and the sacrificial agent are described. With their tunable absorption range and defined energy-band structure, the small-molecule organic semiconductors could offer a new class of metal-free and visible light-active photocatalysts for chemical reactions.
- Wang, Lei,Huang, Wei,Li, Run,Gehrig, Dominik,Blom, Paul W. M.,Landfester, Katharina,Zhang, Kai A. I.
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supporting information
p. 9783 - 9787
(2016/08/10)
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- Visible light mediated reductions of ethers, amines and sulfides
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Visible light-mediated photoredox catalysis enables the chemoselective reduction of activated carbon–heteroatom bonds as a function of reduction potential. The expansion of the scope of C–X bond reductions towards less activated motifs, such as ethers, amines and sulfides, is important to both organic synthesis and macromolecular degradation method development. In the present report, exploration of photoredox catalysis in alcoholic solvents mediated a decrease in the super-stoichiometric use of iPr2NEt and HCO2H in the reduction of α-keto ethers, amines and sulfides. Additionally, in the absence of fragmentation, [Formula presented] bond formation was afforded, suggesting an intermediate ketyl radicals are present in these transformations.
- Monos, Timothy M.,Magallanes, Gabriel,Sebren, Leanne J.,Stephenson, Corey R.J.
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p. 240 - 248
(2016/07/21)
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- Photoinduced Charge-Transfer State of 4-Carbazolyl-3-(trifluoromethyl)benzoic Acid: Photophysical Property and Application to Reduction of Carbon?Halogen Bonds as a Sensitizer
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The photoinduced persistent intramolecular charge-transfer state of 4-carbazolyl-3-(trifluoromethyl)benzoic acid was confirmed. It showed a higher catalytic activity in terms of yield and selectivity in the photochemical reduction of alkyl halides compared to the parent carbazole. Even unactivated primary alkyl bromides could be reduced by this photocatalyst. The high catalytic activity is rationalized by considering the slower backward single-electron transfer owing to the spatial separation of the donor and acceptor subunits.
- Matsubara, Ryosuke,Shimada, Toshiyuki,Kobori, Yasuhiro,Yabuta, Tatsushi,Osakai, Toshiyuki,Hayashi, Masahiko
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supporting information
p. 2006 - 2010
(2016/07/28)
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- Why are organotin hydride reductions of organic halides so frequently retarded? kinetic studies, analyses, and a few remedies
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Kinetic data for reduction of organic halides (RX) by tri-n-butylstannane (SnH) reveal a serious flaw in the current view of the kinetic radical chain: the tacit but unproven assumption that the speed of reaction is determined by the slowest propagation step. Our results show this is rarely true for reductive chains and that the observed rate is in fact controlled by unseen side-reactions of propagating R? and Sn? radicals with the solvent (notably, benzene!) or solvent impurities (e.g., trace benzophenone dryness indicator in THF) or, crucially, with allylic-CH and conjugated unsaturated groups in substrates and products. Most R? and/or Sn? radicals are therefore converted into relatively inert delocalized species A? and/or B? that inhibit the chain. Retardation in the degraded chain is given by a simple sum of terms, each being the ratio of the chain-transfer rate divided by the rate of chain-return. The model kinetic equation is linear and easy to ratify, interpret, and apply: to calculate retarding rate constants, optimize reaction conditions, and identify additives or "remedies" that repair the chain and accelerate reaction. The present work is thus expected to have a helpful impact on the practice and design of SnH radical chain based (and related) syntheses.
- Ingold,Bowry, Vincent W.
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p. 1321 - 1331
(2015/02/19)
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- Method for producing Cyanoacetamide
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Provided is a process for producing cyanoacetic acid esters which achieves high-yield production of cyanoacetic acid esters and minimizes the generation of by-products. A process for producing cyanoacetic acid esters by esterifying cyanoacetic acid with an organic compound represented by the general formula ROH [wherein R is a C1-10 group selected from the group consisting of linear or branched saturated hydrocarbon groups, linear or branched unsaturated hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups and -C2H4-O-R1 groups (wherein R1 is a linear or branched saturated hydrocarbon group, a linear or branched unsaturated hydrocarbon group, an alicyclic hydrocarbon group, or an aromatic hydrocarbon group, each group having 1 to 8 carbon atoms)] in an organic solvent other than the organic compound, wherein both a first solvent, the solubility of cyanoacetic acid in which is 1 [g/100g of solvent] or more at 25°C, and a second solvent which is substantially insoluble in water at 25°C are jointly used as the organic solvent.
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Paragraph 0025
(2016/12/12)
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- Palladium-catalyzed alcoholysis of 3-iodopropynamides: Selective synthesis of carbamoylacetates
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A novel and selective method for the synthesis of carbamoylacetates via the alcoholysis of 3-iodopropynamides has been developed. 3-Iodopropynamides react with alcohols in the presence of palladium(II) acetate and DABCO to afford the corresponding carbamoylacetates in moderate to good yields.
- Tang, Jian-Sheng,Guo, Can-Cheng
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p. 108 - 112
(2015/02/02)
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- 1,5-Diketones Synthesis via Three-Component Cascade Reaction
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A mild and efficient cascade synthesis of 1,5-diketones from readily available N,N-dicyclohexylmethylamine, 1,3-dicarbonyl compounds, and trifluoromethyl β-diketones has been developed. This cascade reaction occurs via an oxidation/Mannich reaction/Cope elimination/Michael addition/retro-Claisen reaction sequence, and provides multiple C-C bond formations in one pot. In addition, exquisite chemoselectivity is achieved in the reaction between 1,3-dicarbonyl compounds and trifluoromethyl β-diketones.
- Xing, Li-Juan,Lu, Tao,Fu, Wei-Li,Lou, Mei-Mei,Chen, Bo,Wang, Zhi-Shen,Jin, Yang,Li, Dan,Wang, Bin
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supporting information
p. 3076 - 3080
(2015/11/03)
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- Transformation of amides into esters by the use of chlorotrimethylsilane
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A mild transformation of various amides and imides into the corresponding esters and diesters in good yields by using chlorotrimethylsilane and alcohols at rt are described. Either primary, secondary, or tertiary amide or imide can be used in this transformation. Primary and secondary alcohols gave better yields than tertiary alcohols.
- Xue, Cuihua,Luo, Fen-Tair
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p. 359 - 362
(2015/02/02)
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- Straightforward synthesis of dihydrobenzofurans and benzofurans from arynes
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Synthesis of dihydrobenzofurans was achieved by a route involving the insertion of arynes into formamides followed by trapping with zinc enolates of α-chlorinated methines. Benzofurans were generated from dihydrobenzofurans having a ketone group via the addition of an ethyl anion, the retro-aldol type reaction, and the elimination of an amino group.
- Yoshioka, Eito,Tanaka, Hidekazu,Kohtani, Shigeru,Miyabe, Hideto
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p. 3938 - 3941
(2013/09/02)
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- Carbene radicals in cobalt(II)-porphyrin-catalysed carbene carbonylation reactions; A catalytic approach to ketenes
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One-pot radicals: Cobalt(III)-carbene radicals, generated by metallo-radical activation of diazo compounds and N-tosylhydrazone sodium salts with cobalt(II) complexes of porphyrins, readily undergo radical addition to carbon monoxide, allowing the catalytic production of ketenes. These ketenes subsequently react with various amines, alcohols and imines in one-pot tandem transformations to produce differently substituted amides, esters and β-lactams in good isolated yields. Copyright
- Paul, Nanda D.,Chirila, Andrei,Lu, Hongjian,Zhang, X. Peter,Debruin, Bas
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supporting information
p. 12953 - 12958
(2013/10/01)
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- First iodine-catalyzed deallylation of reactive allyl methylene esters
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C-Allyl cleavage has been developed using the inexpensive and mild reagent iodine in dimethylsulfoxide. A variety of compounds with active methylene groups were C-deallylated using this reagent. This method is efficient and operationally simple in comparison to the methods using transition-metal complexes. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Nawghare, Beena R.,Lokhande, Pradeep D.
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p. 1955 - 1963
(2013/06/05)
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- Organocatalytic asymmetric annulation of 1,3-bis(alkoxycarbonyl)buta-1,3- dienes and aldehydes
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Asymmetric organocatalytic annulation of E/Z isomeric mixtures of bis(alkyl carboxylate)buta-1,3-dienes and aldehydes has been realized via enamine catalysis. In the presence of α,α-diphenyl-2-pyrrolidinemethanol trimethylsilyl ether, excellent stereo- and enantioselectivities were achieved for a broad spectrum of substrates.
- Pezzati, Bernardo,Chellat, Mathieu F.,Murphy, John J.,Besnard, Celine,Reginato, Gianna,Stephens, John C.,Alexakis, Alexandre
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supporting information
p. 2950 - 2953
(2013/07/26)
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- One-by-one hydrogenation, cross-coupling reaction, and Knoevenagel condensations catalyzed by PdCl2 and the downstream palladium residue
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A novel catalyst-economic strategy with a recovered palladium catalyst was successfully applied for multi-task and maximum reuse in different types of one-by-one downstream reactions, from catalytic hydrogenation to Suzuki and Sonogashira-type cross-coupling reactions, Knoevenagel condensations, and trans-Knoevenagel-like condensations.
- Wang, Hu,Li, Li,Bai, Xing-Feng,Deng, Wen-Hui,Zheng, Zhan-Jiang,Yang, Ke-Fang,Xu, Li-Wen
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supporting information
p. 2349 - 2355
(2013/09/12)
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- Catalyst-free transformations of diethyl 2-ethoxymethylenemalonate and diethyl polyfluorobenzoylmalonates in water
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The unusual transformation of diethyl 2-ethoxymethylenemalonate into triethyl 1,3,5-benzenetricarboxylate is described. This one-pot reaction proceeds in water without any catalyst in a good yield. One of the proposed intermediates of this process is also used under similar conditions to give the desired trisubstituted benzene. A catalyst-free, efficient, practical, and convenient process in water based on deethoxycarbonylation has been developed to form ethyl polyfluorobenzoylacetates in a high yield from diethyl polyfluorobenzoylmalonates.
- Bazhin, Denis N.,Kudyakova, Yulia S.,Burgart, Yanina V.,Saloutin, Victor I.
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supporting information; experimental part
p. 1961 - 1963
(2012/05/19)
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- Catalytic asymmetric conjugate allylation of coumarins
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A catalytic asymmetric conjugate allylation was successfully developed to synthesize potential pharmacologically active 4-allyl-2-oxochroman skeletons. A dual activation strategy was employed by using N,N′-dioxide-Yb(OTf) 3 to activate coumarins and using (CuOTf)2?C 7H8 to activate tetraallyltin via transmetalation, respectively. Good yields and enantioselectivities were obtained under mild conditions.
- Kuang, Yulong,Liu, Xiaohua,Chang, Lu,Wang, Min,Lin, Lili,Feng, Xiaoming
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supporting information; experimental part
p. 3814 - 3817
(2011/09/15)
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- Triphenylphosphane-modified cobalt catalysts for the selective carbonylation of ethyl diazoacetate
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The triphenylphosphane-substituted carbonyl cobalt complexes Co 2(CO)7(PPh3), Co2(CO) 6(CHCO2Et)(PPh3), and [Co(CO) 3(PPh3)2][Co(CO)4] were found to be more effective precatalysts in the carbonylation of ethyl diazoacetate under atmospheric pressure of carbon monoxide at 10 °C in dichloromethane solution than the parent Co2(CO)8 and Co2(CO) 7(CHCO2Et) complexes. The highly reactive (ethoxycarbonyl)ketene is the primary product of the catalytic carbonylation, which dimerizes in the absence of a proper scavenger. In the presence of ethanol as the trapping reagent diethyl malonate is the final product of the carbonylation reaction. The formation of (ethoxycarbonyl)ketene using the catalyst precursor Co2(CO)7(PPh3) occurs in a catalytic cycle, where Co2(CO)6(PPh3) and Co2(CO)6(CHCO2Et)(PPh3) are the repeating species. The 16e species Co2(CO)6(PPh 3) is involved in the deazotization of ethyl diazoacetate, and Co2(CO)6(CHCO2Et)(PPh3) leads to the (ethoxycarbonyl)ketene formation. In the absence of carbon monoxide or at low CO concentration the reaction of Co2(CO)6(CHCO 2Et)(PPh3) with ethyl diazoacetate is the source of Co2(CO)5(CHCO2Et)2(PPh3), which is not an active catalyst for the carbonylation of ethyl diazoacetate. Using [Co(CO)3(PPh3)2][Co(CO)4] as the catalyst precursor, the intermediary formation of [Co(CO) 3(PPh3)2][Co(CO)3(O=C=CHCO 2Et)] through radical pairs is assumed. Substituting PPh3 in Co2(CO)7(PPh3), Co2(CO) 6(CHCO2Et)(PPh3), and [Co(CO) 3(PPh3)2][Co(CO)4] by polymer-bound PPh3 results in active and reusable catalysts for the selective carbonylation of ethyl diazoacetate in dichloromethane solution at 40 °C and 11 bar of pressure with up to 5.1 mol of product/((mol of catalyst) h) turnover frequency.
- Ungvari, Neszta,Foerdos, Eszter,Balogh, Janos,Kegl, Tamas,Parkanyi, Laszlo,Ungvary, Ferenc
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experimental part
p. 3837 - 3851
(2010/12/24)
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- Lewis acid promoted reactions of ethenetricarboxylates with allenes: Synthesis of indenes and γ-lactones via conjugate addition/cyclization reaction
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(Figure presented) Indenes are important core structures in organic chemistry. Few simple arylallenes have been used to construct indene skeletons by Friedel-Crafts reaction. Lewis acid catalyzed reaction of ethenetricarboxylates 1 and arylallenes has been examined in this study. The reaction of arylallenes and ethenetricarboxylate triesters with SnCl4 gave indene derivatives efficiently, via a conjugate addition/Friedel-Crafts cyclization reaction. On the other hand, the reactions of 1,1-diethyl 2-hydrogen ethenetricarboxylate and arylallenes or alkylallenes with SnCl4 at -78 °C or room temperature and subsequent treatment with Et3N gave γ-lactones. The reactions of triethyl ethenetricarboxylate and 1,1-dialkylallenes with SnCl4 at room temperature also gave γ-lactones.
- Yamazaki, Shoko,Yamamoto, Yuko,Fukushima, Yugo,Takebayashi, Masachika,Ukai, Tetsuma,Mikata, Yuji
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supporting information; experimental part
p. 5216 - 5222
(2010/09/05)
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- A versatile synthesis of annulated carbazole analogs involving a domino reaction of bromomethylindoles with arenes/heteroarenes
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A ZnBr2-mediated arylation of aryl/heteroaryl methyl bromides with arenes at 80°C led to the formation of arylated products, which underwent subsequent 1,5-sigmatropic rearrangement followed by electrocyclization and aromatiza tion with loss of a diethylmalonate unit to afford the corresponding annulated products.
- Dhayalan, Vasudevan,Clement, J. Arul,Jagan, Radhakrishnan,Mohanakrishnan, Arasambattu K.
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body text
p. 531 - 546
(2009/09/06)
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- INHIBITORS OF DIACYLGLYCEROL O-ACYLOTRANSFERASE TYPE 1 ENZYME
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Compounds of formula (I), or a pharmaceutically acceptable salt, prodrug, salt of a prodrug, or a combination thereof. Pharmaceutical compositions of formula (I) and related methods for treating or preventing metabolic diseases or conditions.
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Page/Page column 60
(2008/12/06)
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- One-pot organocatalytic domino michael/α-alkylation reactions: Direct catalytic enantioselective cyclopropanation and cyclopentanation reactions
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The development of one-pot organocatalytic domino Michael/α- alkylation reactions between bromomalonates or bromoacetoacetate esters and α,β-unsaturated aldehydes is presented. The chiral-amine-catalyzed reactions with bromomalonates as substrates give access to the corresponding 2-formylcyclopropane derivatives in high yields with excellent diastereoselectivity and up to 99% ee. The catalytic domino Michael/α- alkylation reactions between 4-bromo-acetoacetate and enals provide a route for the synthesis of functionalized cyclopentanones in good to high yields with 93-99 % ee. The products from the organocatalytic reactions were also reduced with high diastereoselectivity to the corresponding cyclopropanols and cy-clopentanols, respectively. Moreover, one-pot combinations of amine and heterocyclic carbene catalysis (AHCC) enabled the highly enantioselective synthesis of β-malonate esters (91-97% ee) from the reaction between bromomalonates and enals. The tandem catalysis included the catalytic domino reaction followed by catalytic in situ chemoselective ring-opening of the 2-formylcyclopropane intermediates.
- Ibrahem, Ismail,Zhao, Gui-Ling,Rios, Ramon,Vesely, Jan,Sunden, Henrik,Dziedzic, Pawel,Cordova, Armando
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scheme or table
p. 7867 - 7879
(2009/09/06)
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- A one pot synthesis of annulated carbazole analogs
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A ZnBr2-mediated arylation of N-protected 2/3-bromomethylindoles containing an electron-deficient malonylidene unit with arenes at 80 °C led to the formation of arylated products, which on unprecedented 1,5-sigmatropic rearrangement followed by electrocyclization and subsequent aromatization with loss of diethylmalonate furnished the corresponding annulated carbazoles in reasonable yields.
- Mohanakrishnan, Arasambattu K.,Dhayalan, Vasudevan,Arul Clement,Sureshbabu, Ramalingam Balamurugan Radhakrishnan,Senthil Kumar, Natarajan
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scheme or table
p. 5850 - 5854
(2009/04/06)
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- Ionic liquid promoted selective debromination of α-bromoketones under microwave irradiation
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The debromination of α-bromoketones with an easily accessible ionic liquid, 1-methyl-3-pentylimidazolium tetrafluoroborate, [pmIm]BF4 under microwave irradiation has been investigated. By controlling the reaction time gem-α-dibromoketones are selectively debrominated to either monobromo or debromoketones. The α-monobromo- and α-monoiodoketones are dehalogenated while the corresponding chloroketones remain inert. The activated vic-bromoacetates are converted to the corresponding (E)-alkenes by the same procedure. These reactions do not require any organic solvent, any metal or any conventional reducing agent. The ionic liquid works here as catalyst as well as reaction medium and is recycled without any appreciable loss of its catalytic efficiency.
- Ranu, Brindaban C.,Chattopadhyay, Kalicharan,Jana, Ranjan
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p. 155 - 159
(2007/10/03)
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- Nucleophilic substitution accompanying carbon-carbon bond cleavage assisted by a nitro group
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A 2-nitrated 3-oxoester reacted with amines or alcohols to afford unsymmetrical malonic acid derivatives as a result of nucleophilic substitution accompanying C-C bond cleavage. The 2-nitrated 3-oxoester easily formed ammonium salts with amines. When the amine is liberated from the salt under equilibrium, nucleophilic amine and electrophilic keto ester locate close to each other. This intimate pair effect causes a pseudo intramolecular reaction to occur, giving rise to effective substitution under mild conditions.
- Nakaike, Yumi,Taba, Noriko,Itoh, Shinobu,Tobe, Yoshito,Nishiwaki, Nagatoshi,Ariga, Masahiro
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experimental part
p. 2413 - 2417
(2009/09/08)
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