- Oxidation of Diols to Lactones by Nocardia corallina B-276
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Several synthetically useful achiral and chiral lactones with high optical purity were prepared by whole-cell oxidation of diols with Nocardia corallina.The absolute stereochemistry of the newly created stereogenic centers was established by comparison with known compounds.In all cases the products were derived fron the oxidation of the pro-S hydroxymethylene group.
- Luna, Hector,Prasad, Kapa,Repic, Oljan
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- Synthesis of surfactants from furfural derived 2[5H]-furanone and fatty amines
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Furfural was oxidized to 2[5H]-furanone 2 using hydrogen peroxide. Furanone 2 was transformed with two equivalents of fatty amines. A condensation and a Michael reaction occurred. Ethyl bromoacetate 5 or methyl acrylate 6 were then added to the secondary amine function. Saponification of the ester function leads to amphoteric surfactants 8a,b,c and 10a,b,c possessing two n-alkyl chains as hydrophobic part. The resulting products can also be considered as Gemini surfactants or twin-tail amphoteric surfactants. Biodegradation studies have been performed on these compounds and the surfactant properties of 8a have been determined in detail.
- Gassama, Abdoulaye,Ernenwein, Cedric,Hoffmann, Norbert
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- Reactions of complex ligands Part 91. Application of ring closing metathesis to Fischer-type carbene complexes: Synthesis and structure of medium-sized chromium oxacycloalkenylidenes
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Six- and seven-membered pentacarbonyl(2-oxacycloalkenylidene) chromium complexes 17 and 6 have been synthesized in moderate to good yields from alkenyloxy(methyl)carbene complex precursors applying an α-alkylation/ruthenium based ring closing metathesis sequence. The ring-closure is hampered for β-alkylated vinylcarbene complexes which may undergo competing intermolecular cross metathesis at the alkenyloxy terminus in low yield.
- Sültemeyer, Jan,D?tz, Karl Heinz,Hupfer, Heike,Nieger, Martin
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- No-D NMR (No-Deuterium Proton NMR) spectroscopy: A simple yet powerful method for analyzing reaction and reagent solutions
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(Equation presented) The title technique is a convenient and powerful method for directly monitoring or assaying any reaction mixture or reagent solution. Examples of some common processes (Fischer esterification, lithiation, butyllithium/THF compatibility, olefin metathesis, and a quantification assay), each interrogated in its native solvent, are presented. The spectral data are easy to acquire, and the information content makes a compelling case for routine use of No-D NMR spectroscopy.
- Hoye, Thomas R.,Eklov, Brian M.,Ryba, Troy D.,Voloshin, Mikhail,Yao, Letitia J.
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- Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal
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The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r
- Zhan, Huan,Cui, Heping,Yu, Junhe,Hayat, Khizar,Wu, Xian,Zhang, Xiaoming,Ho, Chi-Tang
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- Photocatalytic valorization of furfural to value-added chemicals via mesoporous carbon nitride: a possibility through a metal-free pathway
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Strategizing the exploitation of renewable solar light could undoubtedly provide new insight into the field of biomass valorization. Therefore, for the first time, we reported a heterogeneous photocatalytic oxidation route of renewable furfural (FUR) to produce industrial feedstocks maleic anhydride (MAN) and 5-hydroxy-2(5H)-furanone (HFO) under simulated solar light (AM 1.5G) using molecular oxygen (O2) as a terminal oxidant and mesoporous graphitic carbon nitride (SGCN) as a photocatalyst. SGCN showed an excellent photoconversion (>95%) of FUR with 42% and 33% selectivity to MAN and HFO, respectively. Moreover, an excellent selectivity towards MAN (66%) under natural sunlight indicates a pioneering route for the sustainable production of MAN. In addition, the underlying mechanistic route of the FUR photo-oxidation was investigated via various experiments including scavenger studies, substrate studies, and electron spin resonance (ESR) studies which constructively proved the pivotal role of singlet oxygen (1O2) and holes (h+) in FUR photo-oxidation.
- Battula, Venugopala R.,Chauhan, Deepak K.,Giri, Arkaprabha,Kailasam, Kamalakannan,Patra, Abhijit
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p. 144 - 153
(2022/01/19)
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- The effect of Br- and alkali in enhancing the oxidation of furfural to maleic acid with hydrogen peroxide
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This study was focused on investigating a novel catalytic system for the selective conversion of furfural to maleic acid (MA) in an aqueous system with hydrogen peroxide as an oxidant. A series of experiments that study the impacts of catalyst species, furfural concentration, catalyst dosage, reaction temperature, residue time, hydrogen peroxide concentration, excess water content, and solvent types on the oxidation of furfural to MA was carried out. The results showed that the co-existence of Br- and alkali sites might play a vital role in furfural oxidation, which could improve the MA yield remarkably. Under 90 °C for 3 h, 72.4 % MA yield was obtained with KOH and KBr as co-catalyst in an aqueous phase. Moreover, a possible reaction pathway of furfural oxidation was proposed on the basis of our reaction system.
- Yang, Tao,Li, Wenzhi,Ogunbiyi, Ajibola T.
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- A Divergent Paired Electrochemical Process for the Conversion of Furfural Using a Divided-Cell Flow Microreactor
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Furfural is a prominent, non-petroleum-based chemical feedstock material, derived from abundantly available hemicellulose. Hence, its derivatization into other useful biobased chemicals is a subject of high interest in contemporary academic and industrial research activities. While most strategies to convert furfural require energy-intensive reaction routes, the use of electrochemical activation allows to provide a sustainable and green alternative. Herein, a disparate approach for the conversion of furfural is reported based on a divergent paired electrochemical conversion, enabling the simultaneous production of 2(5H)-furanone via an anodic oxidation, and the generation of furfuryl alcohol and/or hydrofuroin via a cathodic reduction. Using water as solvent and NaBr as supporting electrolyte and electron-mediator, a green and sustainable process was developed, which maximizes productive use of electricity and minimizes byproduct formation.
- Cao, Yiran,Knijff, Jasper,Delparish, Amin,d'Angelo, Maria Fernanda Neira,Noёl, Timothy
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p. 590 - 594
(2020/12/25)
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- Chiral Bicyclic Imidazole-Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters
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Utilizing a chiral bicyclic imidazole organocatalyst and adopting a continuous injection process, an alternative route has been developed for the efficient synthesis of chiral phthalidyl ester prodrugs via dynamic kinetic resolution of 3-hydroxyphthalides through enantioselective acylation (up to 99 % ee). The computational studies suggest a general base catalytic mechanism differing from the widely accepted nucleophilic catalytic mechanism. The structure analysis of the key transition states shows that the CH-π interactions and not the previously considered cation/π-π interactions between the catalyst and substrate is the dominant factor giving rise to the observed stereocontrol.
- Zhou, Muxing,Gridneva, Tatiana,Zhang, Zhenfeng,He, Ende,Liu, Yangang,Zhang, Wanbin
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supporting information
p. 1641 - 1645
(2020/11/30)
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- Metal Sub-nanoclusters Confined within Hierarchical Porous Carbons with High Oxidation Activity
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Metal sub-nanoclusters (SNCs) have shown great promise for a variety of catalytic reactions. However, the fabrication of stable metal SNCs simultaneously with high dispersion and high metal contents remains a challenge. Herein, we report a novel and versatile strategy for the synthesis of various bimetal SNCs stabilized within hierarchical porous carbons (HPC). This facile synthesis only involves the self-assembly of a metal-organic framework (MOF) as the precursor, a molten salt assisted pyrolysis process and the final metal replacement. The metal SNCs (mostly less than 0.8 nm) derived from the metal nodes of the MOF are exclusively confined and homogeneously dispersed throughout the organic ligands derived HPC at high loadings (up to 11.2 wt %). The obtained Cu-Pd@HPC composite exhibits superior catalytic activity and recycling durability in the selective transformation of furfural to maleic acid, achieving 97.8 % yield of maleic acid with a TOF value as high as 20.1 h?1 under mild conditions. DFT calculations reveal that the introduction of Pd shifts the partial density of states of Cu toward the Fermi level, leading to stronger chemisorption of furfural to enhance the catalytic activity.
- Zhao, Xin,Kong, Xiangpeng,Wang, Fengliang,Fang, Ruiqi,Li, Yingwei
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supporting information
p. 10842 - 10849
(2021/03/16)
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- Catalytic Enantioselective Total Synthesis of (+)-Lycoperdic Acid
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A concise enantio- and stereocontrolled synthesis of (+)-lycoperdic acid is presented. The stereochemical control is based on iminium-catalyzed Mukaiyama-Michael reaction and enamine-catalyzed organocatalytic α-chlorination steps. The amino group was introduced by azide displacement, affording the final stereochemistry of (+)-lycoperdic acid. Penultimate hydrogenation and hydrolysis afforded pure (+)-lycoperdic acid in seven steps from a known silyloxyfuran.
- Kortet, Sami,Claraz, Aurélie,Pihko, Petri M.
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supporting information
p. 3010 - 3013
(2020/04/10)
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- DIMERIC IMMUNO-MODULATORY COMPOUNDS AGAINST CEREBLON-BASED MECHANISMS
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Disclosed are small molecules against cereblon to enhance effector T cell function. Methods of making these molecules and methods of using them to treat various disease states are also disclosed.
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Page/Page column 66
(2020/02/06)
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- Method for preparing 4, 10-dioxabicyclo[5.2. 1.0(2, 6)]decane-8-ene-3-ketone
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The invention discloses a method for preparing 4, 10-dioxabicyclo[5.2. 1.0(2, 6)]decane-8-ene-3-ketone, and belongs to the technical field of organic chemistry. Maleic anhydride is used as a raw material, and is sequentially subjected to a selective reduction reaction and a Diels-Alder reaction to obtain the 4, 10-dioxabicyclo[5.2. 1.0(2, 6)]decane-8-ene-3-ketone. According to the method, the rawmaterials are easy to obtain, the reaction conditions of each step are simple, the side reaction of polymerization of double bonds in the product can be effectively inhibited, verification is carriedout in kilogram-scale reaction or above, and the process batch reproducibility is good.
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Paragraph 0008; 0017-0019; 0028-0032; 0038-0040
(2020/05/30)
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- Hydrogen Peroxide Oxygenation of Furan-2-carbaldehyde via an Easy, Green Method
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Derivatives of 2(5H)-furanone (γ-crotonolactone) are important intermediate synthetic products with a wide range of biological effects that have become widely used in the pharmaceutical industry, medicine, and veterinary medicine, in particular in the prevention and treatment of fish diseases. However, the environmental issue of obtaining these compounds while reducing the negative impact on the surrounding environment remains relevant. This article describes for the first time a method of γ-crotonolactone synthesis that is based on the concept of green chemistry. Synthesis is carried out under mild conditions using nontoxic reagents by furfural oxidation. For the first time, a mixture of hydrogen peroxide and acetic acid was used for the oxidation of furfural in a ratio of 1:0.05. A mixture of organic acids (succinic, maleic, fumaric, formic, and cinnamic acids), obtained as a byproduct in the synthesis of γ-crotonolactone, can be used as a highly effective, ecofriendly organic fertilizer or in a preparation with a stimulating effect.
- Zvarych, Viktor,Nakonechna, Anna,Marchenko, Mykhailo,Khudyi, Oleksii,Lubenets, Vira,Khuda, Lidiia,Kushniryk, Olga,Novikov, Volodymyr
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p. 3114 - 3117
(2019/03/19)
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- A facile synthesis of γ-butenolides via cyclization of 3-alkenoic acids with dimethyl sulfoxide and oxalyl bromide
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The combination of dimethyl sulfoxide and oxalyl bromide was used to accomplish the cyclization of 3-alkenoic acids with the aid of a base to afford γ-butenolides, in which bromodimethylsulfonium salt generated in situ was proposed to serve as a Br+ source.
- Ding, Rui,Liu, Yongguo,Liu, Lei,Li, Huimin,Tao, Sichen,Sun, Baoguo,Tian, Hongyu
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supporting information
p. 3001 - 3007
(2019/08/26)
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- Catalytic Oxidation of VOCs over SmMnO3 Perovskites: Catalyst Synthesis, Change Mechanism of Active Species, and Degradation Path of Toluene
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Highly active samarium manganese perovskite oxides were successfully prepared by employing self-molten-polymerization, coprecipitation, sol-gel, and impregnation methods. The physicochemical properties of perovskite oxides were investigated by XRD, N2 adsorption-desorption, XPS, and H2-TPR. Their catalytic performances were compared via the catalytic oxidation of toluene. The perovskite prepared by self-molten-polymerization possessed the highest catalytic capacity, which can be ascribed to its higher oxygen adspecies concentration (Olatt/Oads = 0.53), higher surface Mn4+/Mn3+ ratio (Mn4+/Mn3+ = 0.95), and best low-temperature reducibility (H2 consumption = 0.27; below 350 °C). The most active catalyst also exhibited good cycling and long-term stability for toluene oxidation. After a multistep cycle reaction and a long-term reaction of 42 h, the toluene conversion maintained above 99.9% at 270 °C. Mechanistic study hinted that lattice oxygen was involved in toluene oxidation. The oxidation reaction was dependent on the synergism of lattice oxygen, adsorbed oxygen, and oxygen vacancies. The degradation pathway of toluene, researched by diffuse reflectance infrared Fourier transform spectroscopy and online mass spectrometry technologies, demonstrated that a series of organic byproducts existed at a relatively low temperature. This work provides an efficient and practical method for selecting highly active catalysts and for exploring the catalytic mechanism for the removal of atmospheric environmental pollution.
- Liu, Lizhong,Sun, Jiangtian,Ding, Jiandong,Zhang, Yan,Jia, Jinping,Sun, Tonghua
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p. 14275 - 14283
(2019/10/17)
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- Highly Active Mn3-xFexO4 Spinel with Defects for Toluene Mineralization: Insights into Regulation of the Oxygen Vacancy and Active Metals
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A series of highly defected Mn3-xFexO4 spinels with different amounts of oxygen vacancies and active metals were successfully synthesized by regulating the insertion of Fe ions into the crystal structure of Mn3O4 via self-polymerizable monomer adjustment of the molten Mn-Fe salt dispersion. The characterization of X-ray diffraction, Raman, scanning electron microscopy, X-ray photoelectron spectroscopy, and N2 adsorption-desorption showed that the doping of Fe increased the lattice defects, oxygen vacancy concentration, specific surface area, mesoporosity, and catalytic properties compared to Cu ions doping. Temperature-programmed reduction with hydrogen and oxygen pulse chemisorption tests determined that the doping level of Fe ions had an important influence on the oxygen vacancy content and the dispersion of active metals on the catalysts' surfaces. For the best Mn-dispersed and most active Mn2.4Fe0.6O4 catalyst, a long-term toluene oxidation measurement running for 120 h of uninterrupted reaction, at the low temperature of 240 °C, high humidity (relative humidity = 100%), and high weight hourly space velocity of 60000 mL·g-1·h-1, was also carried out, which indicated that the catalyst possessed high stability and endurability. Moreover, the continuous oxidation route and internal principle for toluene oxidation were also revealed by the in situ diffuse-reflectance infrared Fourier transform spectroscopy and gas chromatography-mass spectrometry techniques and deep dynamics study.
- Liu, Lizhong,Sun, Jiangtian,Ding, Jiandong,Zhang, Yan,Sun, Tonghua,Jia, Jinping
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supporting information
p. 13241 - 13249
(2019/10/21)
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- Copper-catalyzed carboxylation of unactivated aryl- And alkenylsilanes with carbon dioxide
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A mild synthetic protocol for the preparation of aryl and alkenyl carboxylic acids was developed through a copper-catalyzed carboxylation reaction of organosilanes with carbon dioxide. The key to this process was the fine-tuning of the reactivity and selectivity of the organometallic nucleophile through structural modifications of the silane.
- Kobayashi, Shū,Kondo, Junpei,Yoo, Woo-Jin
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supporting information
p. 1248 - 1250
(2019/10/11)
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- Rearrangements and Tautomeric Transformations of Heterocyclic Compounds in Homogeneous Reaction Systems Furfural–Н2О2–Solvent
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General information on the reactions of furfurals with hydrogen peroxide is given. We have discussed the Baeyer–Villiger rearrangement of furan 2-hydroxyhydroperoxides and tautomeric transformations with proton transfer of 2-hydroxyfuran and β-formylacrylic acid formed in a homogeneous reaction system furfural–Н2О2–solvent under the catalysis with the formed acids. The factors affecting these rearrangements and tautomeric transformations as well as their specificity in comparison with benzene type compounds, and the pathway of the reactions of furan aldehydes with Н2О2 in water have been analyzed. Ketoenol tautomerism of cyclic hemiacetal form of β-formylacrylic acid leading to its transformation into succinic anhydride has been described for the first time.
- Badovskaya,Poskonin
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p. 1568 - 1579
(2018/11/10)
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- Diverted total synthesis of melodorinol analogues and evaluation of their cytotoxicity
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A series of melodorinol analogues were synthesized via a diverted total synthesis approach, leading to structural modifications on several regions of the molecule. Their cytotoxicity was evaluated against five human cancer cell lines (KB, HeLa-S3, MCF-7, HT-29 and A549). Structure-activity relationship studies revealed key parameters that affect the cytotoxicity. In particular, the novel 4-bromo-furanone analogues exhibited greater cytotoxicity compared to the corresponding non-brominated analogues. The stereochemistry at C-6 and the nature of acyl substituents on the C-6 and C-7 hydroxyl groups also play an important role. The most potent analogues exhibit approximately 15-fold higher cytotoxicity towards KB and HeLa-S3 than melodorinol and also show exceptionally high potency against MCF-7, HT-29 and A549 cell lines.
- Khotavivattana, Tanatorn,Khamkhenshorngphanuch, Thitiphong,Rassamee, Kitiya,Siripong, Pongpun,Vilaivan, Tirayut
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p. 2711 - 2715
(2018/06/12)
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- Highly efficient formic acid-mediated oxidation of renewable furfural to maleic acid with H2O2
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Maleic acid and its anhydride are important intermediates in the chemical industry produced on a multimillion tonne-scale annually. The synthesis of maleic acid/anhydride from renewable biomass resources such as furfural and 5-hydroxymethylfurfural is highly desirable for the sustainability of human society. Most of the previously reported processes for maleic acid/anhydride synthesis from biomass suffer from low efficiency, complicated conditions and poor catalyst recyclability. Herein, we demonstrate a highly efficient and simple system for the synthesis of maleic acid from furfural. An excellent yield (95%) of maleic acid was achieved under mild conditions in this very simple system which requires only H2O2 as an oxidant in formic acid solvent. Under similar conditions, an 89% yield of maleic acid was achieved from biomass-derived 5-hydroxymethylfurfural. This study presents a novel synthetic method and a promising process for maleic acid production from renewable biomass resources.
- Li, Xiukai,Ho, Ben,Lim, Diane S. W.,Zhang, Yugen
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supporting information
p. 914 - 918
(2017/08/17)
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- (Meth) acrylic acid ester
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PROBLEM TO BE SOLVED: To provide a method and a catalyst capable of inexpensively manufacturing, in a high yield and in an industrially efficient manner, a (meth)acrylic acid ester including a lactone ring and useful as constituent monomers, etc. of polymer compounds for photoresists and/or (meth)acrylic acid ester including a cyclic skeleton and having an acid-dissociating attribute.SOLUTION: An alcohol having a 5- or 6-membered intra-cyclic ester ring skeleton and (meth)acrylic anhydride are reacted in the presence of an alkali metal salt or alkaline earth metal salt catalyst having an electronegativity of 0.95 or higher.
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Paragraph 0033
(2017/10/26)
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- A γ - tiglyl lactone and synthetic method of derivative thereof
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The invention relates to a synthetic method for gamma-crotonolactone and a derivative thereof. In the synthetic method for the gamma-crotonolactone, the gamma-crotonolactone is prepared from a 2,5-dihydrofuran compound used as a raw material through the hydrolysis reaction; the derivative of the gamma-crotonolactone is alpha-derivative of the gamma-crotonolactone; the alpha-derivative of the gamma-crotonolactone is prepared through performing the Baylis-Hillman reaction on the gamma-crotonolactone. The gamma-crotonolactone and the alpha-derivative thereof have quite wide application in the organic synthetic chemistry and medicinal chemistry. The synthetic method has the advantages that the raw materials are easy to obtain, the reagent is low in price, the route is simple and short, the condition is moderate, the operation is simple, and the industrial production is facilitated.
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Paragraph 0095; 0096; 0097
(2017/08/16)
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- Porous Zirconium–Furandicarboxylate Microspheres for Efficient Redox Conversion of Biofuranics
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Biofuranic compounds, typically derived from C5 and C6 carbohydrates, have been extensively studied as promising alternatives to chemicals based on fossil resources. The present work reports the simple assembly of biobased 2,5-furandicarboxylic acid (FDCA) with different metal ions to prepare a range of metal–FDCA hybrids under hydrothermal conditions. The hybrid materials were demonstrated to have porous structure and acid–base bifunctionality. Zr-FDCA-T, in particular, showed a microspheric structure, high thermostability (ca. 400 °C), average pore diameters of approximately 4.7 nm, large density, moderate strength of Lewis-base/acid centers (ca. 1.4 mmol g?1), and a small number of Br?nsted-acid sites. This material afforded almost quantitative yields of biofuranic alcohols from the corresponding aldehydes under mild conditions through catalytic transfer hydrogenation (CTH). Isotopic 1H NMR spectroscopy and kinetic studies verified that direct hydride transfer was the dominant pathway and rate-determining step of the CTH. Importantly, the Zr-FDCA-T microspheres could be recycled with no decrease in catalytic performance and little leaching of active sites. Moreover, good yields of C5 (i.e., furfural) or C4 products [i.e., maleic acid and 2(5H)-furanone] could be obtained from furfuryl alcohol without oxidation of the furan ring over these metal–FDCA hybrids. The content and ratio of Lewis-acid/base sites were demonstrated to dominantly affect the catalytic performance of these redox reactions.
- Li, Hu,Liu, Xiaofang,Yang, Tingting,Zhao, Wenfeng,Saravanamurugan, Shunmugavel,Yang, Song
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p. 1761 - 1770
(2017/04/27)
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- Non-plasmonic metal nanoparticles as visible light photocatalysts for the selective oxidation of aliphatic alcohols with molecular oxygen at near ambient conditions
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Nanoparticles (NPs) of Pd and Pt were used for the selective oxidation of aliphatic alcohols with molecular oxygen as an oxidant at near ambient temperatures under visible light irradiation. Distinct final products were obtained under identical reaction conditions, aliphatic esters formed over the Pd NPs while aldehydes formed over the Pt NPs. The reason for this different product selectivity is proven to be due to the much stronger interaction of Pd NPs with alcohol and aldehyde compared to Pt NPs. The photocatalytic activity is tuneable by light intensity or a moderate change in the reaction temperature.
- Tana, Tana,Guo, Xiao-Wei,Xiao, Qi,Huang, Yiming,Sarina, Sarina,Christopher, Phillip,Jia, Jianfeng,Wu, Haishun,Zhu, Huaiyong
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p. 11567 - 11570
(2016/10/03)
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- Method for preparing GBL (Gamma-Butyrolactone) by taking furfural as raw material
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The invention discloses a method for preparing GBL (Gamma-Butyrolactone) by taking furfural as a raw material. The method comprises two steps of oxidizing the furfural to prepare 2(5H)-furanone and hydrogenating the 2(5H)-furanone to prepare the GBL, wherein the 2(5H)-furanone can be synthesized by the furfural by taking homogeneous-phase acid or solid acid as a catalyst and taking hydrogen peroxide as an oxidant under the conditions of mild temperature and pressure. The 2(5H)-furanone is further selectively hydrogenated to obtain the GBL under the effect of a metal catalyst in a hydrogen atmosphere. The GBL can be generated by commonly hydrogenating the 2(5H)-furanone serving as a main product and C4 binary acid serving as a byproduct of the oxidation of the furfural in situ under appropriate conditions. According to the method, high-efficiency conversion from the furfural serving as a biomass raw material to the GBL serving as a fine chemical product is realized; the method has a great application prospect.
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Paragraph 0041; 0042
(2016/11/14)
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- But-2-ene-1,4-diamine and But-2-ene-1,4-diol as Donors for Thermodynamically Favored Transaminase- and Alcohol Dehydrogenase-Catalyzed Processes
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Both cis- and trans-but-2-ene-1,4-diamines have been prepared and efficiently applied as sacrificial cosubstrates in enzymatic transamination reactions. The best results were obtained with the cis-diamine. The thermodynamic equilibrium of the stereoselective transamination process is shifted to the amine formation due to tautomerization of 5H-pyrrole into 1H-pyrrole, achieving high conversions (78–99%) and enantiomeric excess (up to >99%) by using a small excess of the amine donor. Furthermore, when the reaction proceeded, a strong coloration was observed due to polymerization of 1H-pyrrole. A structurally related compound, cis-but-2-ene-1,4-diol, has been utilized as cosubstrate in different alcohol dehydrogenase (ADH)-mediated bioreductions. In this case, high conversions (91–99%) were observed due to a lactonization process. Both strategies are convenient from both synthetic and atom economy points of view in the production of valuable optically active products. (Figure presented.).
- Martínez-Montero, Lía,Gotor, Vicente,Gotor-Fernández, Vicente,Lavandera, Iván
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supporting information
p. 1618 - 1624
(2016/10/13)
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- Selective oxidation of furfural in a bi-phasic system with homogeneous acid catalyst
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The selective catalytic oxidation of furfural to 2(5H)-furanone, succinic acid (SA) and maleic acid (MA) was studied. Under optimized conditions, furfural was oxidized to 2(5H)-furanone with a yield of 60–62% in an aqueous/organic bi-phasic system using 1,2-dichloroethane or ethyl acetate as the solvent and formic acid as the catalyst, while the total yield of SA and MA was 15–20%. Compared with other homogeneous and heterogeneous acid catalysts, formic acid gave a much higher selectivity to 2(5H)-furanone because it reacted with hydrogen peroxide to generate performic acid that had a strong oxidizing nature and good solubility in both the aqueous and organic phases. The solvent had a significant influence on the product distribution. A simplified reaction network was established to quantitatively analyze the solvent effect based on the reaction rate constants. In the homogeneous system, the yield of 2(5H)-furanone decreased while the yield of SA increased with an increasing dielectric constant of the solvent. The formic acid/furfural molar ratio, reaction temperature and furfural concentration were optimized for the selective oxidation of furfural to 2(5H)-furanone in the bi-phasic reaction system.
- Li, Xiaodan,Lan, Xiaocheng,Wang, Tiefeng
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- Highly selective catalytic conversion of furfural to γ-butyrolactone
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A two-step process was developed for the production of γ-butyrolactone (GBL) from furfural. Furfural was first oxidized using homogeneous acid catalysts under mild conditions in an aqueous/organic bi-phasic system to obtain 2(5H)-furanone, which was then selectively hydrogenated to GBL with a high yield over supported metal catalysts.
- Li, Xiaodan,Lan, Xiaocheng,Wang, Tiefeng
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supporting information
p. 638 - 642
(2016/02/12)
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- Dicopper Complexes with Anthyridine-Based Ligands: Coordination and Catalytic Activity
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Two new anthyridine-based ligands, 5-phenyl-2,8-bis(2-pyridinyl)-1,9,10-anthyridine (L3) and 5-phenyl-2,8-bis(6′-bipyridinyl)-1,9,10-anthyridine (L4), were designed for accommodation of dimetallic systems with the metal ions separated by 5 ?. Complexation of Cu(ClO4)2 with L3 and L4 provided the corresponding dicopper complexes [{Cu2(L3)(H2O)4(CH3CN)2}(ClO4)4] (3) and [{Cu2(L4)(μ-ClO4)2}(PF6)2] (4), respectively. Both complexes were characterized by spectroscopic methods, and the detail structural features were further confirmed by X-ray crystallography. Structural analyses of 3 and 4 reveal the Cu···Cu distances in the complexes being 4.9612(7) and 5.013 (2) ?, respectively. Both complexes are active in the catalytic oxidation of benzyl alcohols into the corresponding aldehydes. Furthermore, complex 4 appears to be a good catalyst for the oxidative coupling of primary alcohols into the corresponding esters with the use of hydrogen peroxide as the oxidant in an aqueous medium. The possible cooperative interactions between the metal ions during the catalysis are discussed.
- Huang, Da-Wei,Liu, Yi-Hung,Peng, Shie-Ming,Liu, Shiuh-Tzung
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p. 151 - 158
(2016/02/05)
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- Process for treating homoserin compounds
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The present invention relates to the preparation of a useful compound which can be used as an intermediate product for preparing an important compound in the industrial field from a homoserine-based compound and provides a process for treating a homoserine-based compound, capable of simply mass producing a useful compound from a homoserine-based compound with excellent efficiency.(AA) Homoserine-based compound(BB) Product(CC) GBL derivative(DD) Halo-GBL(EE, FF, GG) GBL puranone(HH) Puranone(II) Dialkyl succinate(JJ) Step 1(KK) Step 2(LL) Step 3(MM) Step 4(NN) Step 5(OO) Step 6(PP) Step 7COPYRIGHT KIPO 2016
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Paragraph 0095; 0109-0114
(2017/01/02)
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- Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols
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Cu/nitroxyl catalysts have been identified that promote highly efficient and selective aerobic oxidative lactonization of diols under mild reaction conditions using ambient air as the oxidant. The chemo- and regioselectivity of the reaction may be tuned by changing the identity of the nitroxyl cocatalyst. A Cu/ABNO catalyst system (ABNO = 9-azabicyclo[3.3.1]nonan-N-oxyl) shows excellent reactivity with symmetrical diols and hindered unsymmetrical diols, whereas a Cu/TEMPO catalyst system (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyl-N-oxyl) displays excellent chemo- and regioselectivity for the oxidation of less hindered unsymmetrical diols. These catalyst systems are compatible with all classes of alcohols (benzylic, allylic, aliphatic), mediate efficient lactonization of 1,4-, 1,5-, and some 1,6-diols, and tolerate diverse functional groups, including alkenes, heterocycles, and other heteroatom-containing groups.
- Xie, Xiaomin,Stahl, Shannon S.
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supporting information
p. 3767 - 3770
(2015/04/14)
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- Effect of acid-base properties of the medium on the reactions in the 2-furaldehyde-H2O2-H2O system with and without VOSO4
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Data on the effect of acid-base properties of the medium in the pH range 0-9 on the intensity of transformation of 2-furaldehyde and the direction of the multi-stage reactions in the 2-furaldehyde-H2O2-H 2O system in the presence of VOSO4 and without it are presented. Significant influence of the medium pH value on the reaction pathway in the system under investigation hase been found. Mechanism of these reactions considering the effect of acid-base properties of the medium has been suggested.
- Badovskaya,Poskonin,Ponomarenko
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p. 1133 - 1140
(2014/08/05)
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- Pt nanoparticles over TiO2-ZrO2 mixed oxide as multifunctional catalysts for an integrated conversion of furfural to 1,4-butanediol
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1,4-butanediol (BDO) is an important commodity chemical for manufacturing many basic chemicals and valuable polymers. Its current manufacturing processes are exclusively based on feedstocks derived from oil and natural gas. The biomass-to-BDO chemical transformation is via furfural, a key platform molecule from glucose and xylose. The integrated conversion involves two sequent reaction steps: selective oxidation of furfural to furanones and hydrogenation of the mixture of furanones to BDO. Platinum nanoparticles supported over TiO 2-ZrO2 perform well for both oxidation and hydrogenation steps and the total yield of BDO reaches 85.2%. The chemical composition and crystallinity of the mixed oxide support significantly affect the catalytic performance. The best catalyst is platinum supported over TiO 2-ZrO2 mixed oxide (Ti/Zr, 1:1) calcined at 823 K, which also exhibits good recoverability and recyclability in the five-run test.
- Li, Fengbo,Lu, Tao,Chen, Bingfeng,Huang, Zhijun,Yuan, Guoqing
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p. 252 - 258
(2014/05/20)
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- Poly-(styrene sulphonic acid): An acid catalyst from polystyrene waste for reactions of interest in biomass valorization
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This article reports on the use of poly-(styrene sulphonic acid) (PSSA) prepared by sulphonation of polystryrene waste as catalyst in reactions demanding acid sites. Two different waste derived catalysts (waste to catalyst, WTC) were studied: soluble PSSA (WTC-PSSA) and solid SiO2-PSSA nanocomposite (WTC-SiO2-PSSA). The catalytic properties of these waste derived acid catalysts have been explored in three different reactions of interest in biomass valorization: biodiesel synthesis, xylose dehydration to furfural and furfural oxidation to maleic and succinic acids. The results show that both soluble and nanocomposite WTC catalysts present promising catalytic properties. The WTC-PSSA requires ultrafiltration for reutilization whereas the WTC-SiO2-PSSA can be separated from the reaction mixtures by more usual techniques (centrifugation or conventional filtration). Further research is required for improving the hydrothermal stability of WTC-SiO2-PSSA in order to substantially reduce the leaching of polymer that takes place during the catalytic runs.
- Alonso-Fagúndez,Laserna,Alba-Rubio,Mengibar,Heras,Mariscal,Granados, M. López
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p. 285 - 294
(2014/07/07)
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- Aqueous-phase catalytic oxidation of furfural with H2O2: High yield of maleic acid by using titanium silicalite-1
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This investigation explores the selective liquid-phase oxidation of furfural to maleic acid (MA) using hydrogen peroxide as an oxidant and titanium silicalite (TS-1) as a catalyst. The effect of temperature and of the concentration of H2O2, furfural and catalyst on the MA yield was studied. The highest yield, 78 mol%, was obtained under the following reaction conditions: 4.6 wt% of furfural, 4.6 wt% of catalyst, a H2O2/furfural mol ratio of 7.5, corresponding to 12.3 wt% of H2O2, 323 K and 24 hours of reaction. To reduce the amount of H2O2 employed, a two-step sequence of reactions was conducted using TS-1 and Amberlyst 70 consecutively as catalysts in the first and second steps, respectively. In this case, a H2O2/furfural mol ratio = 4.4 was required, which is quite close to the stoichiometric ratio (3.0), and a maleic acid yield close to 80% was obtained under 4.6 wt% of furfural, 4.6 wt% of catalyst and 28 h of reaction at 323 K; after 52 h of reaction, the MA yield reached 92%. Fresh and used catalysts were characterised by X-ray diffraction (XRD), Raman spectroscopy, total reflection X-ray fluorescence (TXRF), X-ray photoelectron spectroscopy (XPS), N2 adsorption-desorption isotherms and thermogravimetric analysis. Ti was largely incorporated within the silicalite framework, but the presence of some TiO2 anatase was also confirmed. Ti leaching was observed, especially during the first run but became much less important in successive cycles. Leaching affects both anatase and Ti species within the silicalite framework. Notwithstanding the leaching, when using pure furfural, TS-1 could be reused for six runs without noticeable deactivation, whereas when using furfural directly derived from biomass, weak but visible deactivation occurred upon reutilisation; this deterioration must be related to the presence of some organic products other than furfural.
- Alonso-Fagndez,Agirrezabal-Telleria,Arias,Fierro,Mariscal,Granados, M. Lpez
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p. 54960 - 54972
(2015/02/19)
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- A novel one-pot sulfonyloxylactonization of alkenoic acids mediated by hypervalent iodine species generated in situ from ammonium iodide
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A novel and efficient one-pot procedure was designed for the sulfonyloxylactonization of alkenoic acids by the reaction of alkenoic acids with m-chloroperbenzoic acid and sulfonic acids in the presence of a catalytic amount of ammonium iodide in a mixture acetonitrile/2,2,2-trifluoroethanol (4: 1) at room temperature for 24 h, which provided the corresponding sulfonyloxy lactones in moderate-to-good yields. Copyright
- Hu, Jiantao,Zhu, Min,Xu, Yuan,Yan, Jie
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p. 137 - 145
(2014/02/14)
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- Asymmetric total syntheses of (-)-penicipyrone and (-)-tenuipyrone via biomimetic cascade intermolecular michael addition/cycloketalization
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The first total syntheses of (-)-penicipyrone and (-)-tenuipyrone were accomplished enantioselectively in 12 steps with an 11% yield and 6 steps with a 28% yield from the known 4-((tert-butyldimethylsilyl)oxy)-cyclopent-2-enone, respectively, by developing a biomimetic bimolecular cascade cyclization featuring an intermolecular Michael addition/cyclo-(spiro-)ketalization sequence. The relative, absolute stereochemistry and carbon connectivity of penicipyrone was further confirmed by X-ray crystallographic analysis and comparison of optical rotations.
- Song, Liyan,Yao, Hongliang,Zhu, Liangyu,Tong, Rongbiao
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supporting information
p. 6 - 9
(2013/03/28)
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- Rate coefficients for the gas-phase reactions of chlorine atoms with cyclic ethers at 298 K
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Rate coefficients of reactions of Cl atoms with cyclic ethers, tetrahydropyran (THP), tetrahydrofuran (THF), and dihydrofurans (2,5-DHF and 2,3-DHF) have been measured at 298 K using a relative rate method. The relative rate ratios for THP and THF are 0.80 ± 0.05 and 0.80 ± 0.08, respectively, with n-hexane as the reference molecule. The relative rate ratios for THF and 2,5-DHF with n-pentane as the reference molecule are 0.95 ± 0.07 and 1.73 ± 0.06, respectively, and for 2,5-DHF with 1-butene as reference is 1.38 ± 0.05. The average values of the rate coefficients are (2.52 ± 0.36), (2.50 ± 0.39), and (4.48 ± 0.59) × 10-10 cm3 molecule-1 s-1 for THP, THF, and 2,5-DHF, respectively. The errors quoted here for relative rate ratios are 2σ of the statistical variation in different sets of experiments. These errors, combined with the reported errors of the reference rate coefficients using the statistical error propagation equation, are the quoted errors for the rate coefficients. In the case of 2,3-DHF, after correcting for the dark reaction with CH3COCl and assuming no interference from other radical reactions, a relative rate ratio of 0.85 ± 0.16 is obtained with respect to cycloheptene, corresponding to a rate coefficient of (4.52 ± 0.99) × 10-10 cm3 molecule-1 s-1. Unlike cyclic hydrocarbons, there is no increase with increasing number of CH2 groups in these cyclic ethers whereas there is an increase in the rate coefficient with unsaturation in the ring. An attempt is also made to correlate the rate coefficients of cyclic hydrocarbons and ethers with the molecular size as well as HOMO energy.
- Alwe,Walawalkar,Sharma,Pushpa,Dhanya,Naik
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p. 295 - 305
(2013/08/25)
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- Expanding the scope of biomass-derived chemicals through tandem reactions based on oxorhenium-catalyzed deoxydehydration
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New modes of DODH: Oxorhenium compounds act as deoxydehydration(DODH)/acid dual-purpose catalysts to transform biomass-derived diol substrates into a variety of commodity chemical precursors. The power of this approach is highlighted by a tandem [1,3]-OH shift/DODH of 2-ene-1,4-diols and 2,4-diene-1,6-diols, and by a DODH/esterification sequence of sugar acids to unsaturated esters for the production of polymers and plasticizers. Copyright
- Shiramizu, Mika,Toste, F. Dean
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supporting information
p. 12905 - 12909
(2014/01/06)
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- Highly efficient aqueous oxidation of furfural to succinic acid using reusable heterogeneous acid catalyst with hydrogen peroxide
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Green oxidation of inedible biomass-based 2-furaldehyde (furfural) to succinic acid (SA), one of the most important building blocks, was successfully achieved using Amberlyst-15 as a reusable solid acid catalyst in water at 353K in the presence of hydrogen peroxide (H2O2).
- Choudhary, Hemant,Nishimura, Shun,Ebitani, Kohki
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supporting information; scheme or table
p. 409 - 411
(2012/06/01)
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- Mukaiyama-Michael reactions with acrolein and methacrolein: A catalytic enantioselective synthesis of the C17-C28 fragment of pectenotoxins
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Enantioselective iminium-catalyzed reactions with acrolein and methacrolein are rare. A catalytic enantioselective Mukaiyama-Michael reaction that readily accepts acrolein or methacrolein as substrates, affording the products in good yields and 91-97% ee, is presented. As an application of the methodology, an enantioselective route to the key C17-C28 segment of the pectenotoxin using the Mukaiyama-Michael reaction as the key step is described.
- Kemppainen, Eeva K.,Sahoo, Gokarneswar,Valkonen, Arto,Pihko, Petri M.
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supporting information; experimental part
p. 1086 - 1089
(2012/03/27)
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- Facile and highly diastereoselective synthesis of 3-aminooxindoles via AgOAc-catalyzed vinylogous Mannich reaction
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A novel AgOAc-catalyzed vinylogous Mannich reaction between easily prepared imines 1 derived from isatins and trimethylsilyloxyfuran 2 (TMSOF) was developed. This method provided a facile synthetic route to get access to synthetically useful quaternary 3-aminooxindole in excellent yields (94-99%) and diastereoselectivities (>99:1).
- Shi, Yu-Hua,Wang, Zheng,Shi, Ying,Deng, Wei-Ping
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experimental part
p. 3649 - 3653
(2012/06/18)
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- Synthesis and insecticidal activity of an oxabicyclolactone and novel pyrethroids
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Deltamethrin, a member of the pyrethroids, one of the safest classes of pesticides, is among some of the most popular and widely used insecticides in the World. Our objective was to synthesize an oxabicyclolactone 6 and five novel pyrethroids 8-12 from readily available furfural and D-mannitol, respectively, and evaluate their biological activity against four insect species of economic importance namely A. obtectus, S. zeamais, A. monuste orseis, and P. americana. A concise and novel synthesis of 6,6-dimethyl-3- oxabicyclo[3.1.0]hexan-2-one (6) from furfural is described. Photochemical addition of isopropyl alcohol to furan-2(5H)-one afforded 4-(1'-hydroxy-1'-methylethyl)tetrahydrofuran- 2-one (3). The alcohol 3 was directly converted into 4-(1'-bromo-1'-methylethyl)- tetrahydrofuran-2-one (5) in 50% yield by reaction with PBr3 and SiO2. The final step was performed by cyclization of 5 with potassium tert-butoxide in 40% yield. The novel pyrethroids 8-12 were prepared from methyl (1S,3S)-3-formyl-2, 2-dimethylcyclopropane- 1-carboxylate (7a) by reaction with five different aromatic phosphorous ylides. Compounds 6-12 presented high insecticidal activity, with 6 and 11 being the most active. Compound 6 killed 90% of S. zeamais and 100% of all the other insects evaluated. Compound 11 killed 100% of all insects tested.
- De Alvarenga, Elson S.,Carneiro, Vania M. T.,Resende, Gabriela C.,Picanco, Marcelo C.,De Sa Farias, Elizeu,Lopes, Mayara Cristina
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p. 13989 - 14001
(2013/02/26)
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- Water-promoted one-pot vinylogous Mannich-type reaction of trimethylsilyloxyfuran
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Water, produced in situ during the formation of imines from aldehydes 1 and amines 2, is employed to promote the one-pot Mannich reaction of trimethylsilyloxyfuran 3a without addition of extra solvent or catalyst. This clean and quick reaction allows the obtention of a series of 5-substituted γ-butenolides 4 with good yields and modest diastereomeric ratio. A large panel of substituents is tolerated ranging from aliphatic chains to aromatic or heteroaromatic rings.
- Landelle, Grégory,Claraz, Aurélie,Oudeyer, Sylvain,Levacher, Vincent
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body text
p. 2414 - 2416
(2012/06/01)
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- Novel catalytic bromolactonization of alkenoic acids using iodobenzene and Oxone
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The novel catalytic reaction for bromolactonization of alkenoic acids is reported. When iodobenzene is used as recyclable catalyst in combination with Oxone as terminal oxidant, the cyclization of various 4-pentenoic acids with sodium bromide is easily carried out in CF3CH2OH at room temperature and giving five-membered bromolactones in good yields.
- He, Yan,Pu, Ye,Shao, Bo,Yan, Jie
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experimental part
p. 695 - 698
(2011/07/30)
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- Study on the bromolactonisation of alkenoic acids with (diacetoxyiodo) benzene
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A study on the bromolactonisation of alkenoic acids is reported. When various pent-4-enoic acids reacted with (diacetoxyiodo)benzene (DIB) and lithium bromide in CH3OH at room temperature, most of the five-membered bromolactones were obtained in good to excellent yields in short times. Some had two diastereoisomers. When but-3-enoic acid and trans-hex-3-enoic acid were treated under the same conditions, only unsaturated lactones were found after workup. When hex-5-enoic acid was subjected to the same conditions, however, the desired six-membered bromolactone was not successfully separated.
- He, Yan,Yang, Zhenping,Yan, Jie
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experimental part
p. 167 - 169
(2010/07/08)
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- A novel camphorsulfonyloxylactonization of alkenoic acids
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(Chemical Equation Presented) The novel reaction of [hydroxyl (((+)-10-camphorsulfonyl)oxy)iodo]benzene (1) with alkenoic acids was reported. When 1 reacted with various 4-pentenoic acids in CH3CN, camphorsulfonylactons were obtained in excellent yields in short times, some had two diastereoisomers, whereas 1 reacted with 5-hexenoic acid, giving middle yield of camphorsulfonylacton; however, 3-butenoic and trans-3-hexenoic acids reacted with 1 slowly in CH2Cl2, only unsaturated lactones were provided.
- Zhu, Min,Sun, Na-Bo,Li, He,Yan, Jie
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experimental part
p. 436 - 440
(2010/06/16)
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- A convenient phosphoryloxylactonization of pentenoic acids with catalytic hypervalent iodine(III) reagent
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A novel and convenient catalytic method for phosphoryloxylactonization of pentenoic acids is available: the cyclization of 4-pentenoic acids with phosphates using iodobenzene as a recyclable catalyst in combination with m-chloroperbenzoic acid as the terminal oxidant was easily carried out in CF3CH2OH at room temperature, giving phosphoryloxylactons in good yields, some of them had two diastereoisomers.
- Zhou, Zhong-Shi,He, Xue-Han
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experimental part
p. 2480 - 2482
(2010/06/14)
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- Catalytic oxidation reactions of furan and hydrofuran compounds 9. Characteristics and synthetic possibilities of the reaction of furan with aqueous hydrogen peroxide in the presence of compounds of niobium(II) and (V)
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The effect of the catalytic characteristics of compounds of niobium(II) and (V) on the duration and the composition of the products during the oxidation of furfural by aqueous hydrogen peroxide was studied. It was established that the process is intermediate in its main characteristics between reactions of the compounds taking place under the conditions of autocatalysis by the acids that are formed and in the presence of the vanadium compounds. The main product of the reaction is 2(5H)-furanone. A method is proposed for its production with yields of up to 60%.
- Poskonin
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experimental part
p. 1177 - 1183
(2010/05/02)
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- An efficient catalytic sulfonyloxylactonization of alkenoic acids using hypervalent iodine(III) reagent
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A novel and efficient catalytic method for sulfonyloxylactonization of alkenoic acids is reported. (Diacetoxyiodo)benzene could be used as a recyclable catalyst in combination with m-chloroperbenzoic acid as an oxidant in the presence of sulfonic acid to
- Yan, Jie,Wang, Hong,Yang, Zhenping,He, Yan
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experimental part
p. 2669 - 2672
(2010/01/07)
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- Allylic Oxidations Catalyzed by Dirhodium Catalysts under Aqueous Conditions
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The present invention relates to compositions and methods for achieving the efficient allylic oxidation of organic molecules, especially olefins and steroids, under aqueous conditions. The invention concerns the use of dirhodium (II,II) “paddlewheel complexes, and in particular, dirhodium carboximate and tert-butyl hydroperoxide as catalysts for the reaction. The use of aqueous conditions is particularly advantageous in the allylic oxidation of 7-keto steroids, which could not be effectively oxidized using anhydrous methods, and in extending allylic oxidation to enamides and enol ethers.
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Page/Page column 24
(2009/04/24)
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- Supported gold nanoparticles as a reusable catalyst for synthesis of lactones from diols using molecular oxygen as an oxidant under mild conditions
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The oxidative lactonization of various diols using molecular oxygen as a primary oxidant can be efficiently catalyzed by hydrotalcite-supported Au nanoparticles (Au/HT). For instance, lactonization of 1,4-butanediol gave γ-butyrolactone with an excellent turnover number of 1400. After lactonization, the Au/HT can be recovered by simple filtration and reused without any loss of its activity and selectivity.
- Mitsudome, Takato,Noujima, Akifumi,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
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experimental part
p. 793 - 797
(2010/04/23)
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