- Polyoxovanadate catalysts for oxidation of 1-phenyl ethanol: From the discrete [V4O12]4- and [V10O28]6- anions to the anionic [V6O17]:N4 n - Coordination polymer
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Three polyoxovanadate-based hybrids {[Ru(phen)3]2[V4O12]}·13H2O (1), [Ru(phen)3]2[V10O28]·15H2O (2), and [Ru(phen)3]2[V6O17]Cl·11H2O (3) (phen = 1,10-phenanthroline) were prepared under hydrothermal conditions and characterized by electron paramagnetic resonance (EPR) spectroscopy, infrared spectroscopy (IR), powder X-ray diffraction (PXRD), thermogravimetric (TG) analysis, X-ray photoelectron spectroscopy (XPS), and single crystal X-ray diffraction analysis. Although the structures of both the cyclic vanadate [V4O12]4- and the [V10O28]6- anions are well-known, interestingly, a novel 1-dimensional (1-D) coordination polymer [V6O17]n4n- anion was constructed from tetranuclear [V4O12]4- and dinuclear [V2O7]4- building blocks, which were linked alternately through corner-shared oxygen atoms. Furthermore, the negative charges of polyoxovanadate [V4O12]4-, [V10O28]6- and [V6O17]4- anions were balanced by two [Ru(phen)3]2+/3+ complex cations. The catalytic properties of compounds 1-3 for the oxidation of 1-phenyl ethanol by tert-butyl hydroperoxide (TBHP) were investigated, and the results demonstrated that 1 and 3 exhibited excellent catalytic activities for the oxidation of 1-phenyl ethanol under mild catalytic conditions.
- Wang, Ke,Xu, Qiaofei,Ma, Pengtao,Zhang, Chao,Wang, Jingping,Niu, Jingyang
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- Nonselective bromination-selective debromination strategy: Selective bromination of unsymmetrical ketones on singly activated carbon against doubly activated carbon
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(Matrix presented) We have found a new synthetic method for the preparation of the α-bromoketones that are brominated in the less activated terminal position of unsymmetrical ketones. Brominations in short reaction times (kinetically controlled) provided internally brominated compounds as a major product. However, brominations in longer reaction times (thermodynamically controlled) gave more of the terminally brominated compound through the reversible reaction by Br2 and produced hydrogen bromide. Several brominated compounds at the terminal position were successfully prepared through the new synthetic route.
- Choi, Han Young,Chi, Dae Yoon
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- Ortho Enhancement in the Ozone-Mediated Nitration of Some Aromatic Carbonyl Compounds with Nitrogen Dioxide
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Alkyl aryl ketones react smoothly with nitrogen dioxide at low temperatures in the presence of ozone to give a mixture of ortho and meta nitration products (o/m = 1.1-3.8/1.0), the former becoming predominant with the increasing size of alkyl moiety.
- Suzuki, Hitomi,Murashima, Takashi,Tatsumi, Atsuo,Kozai, Iku
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- meta-nitroacetophenone at 173 K
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The title compound, methyl 2-nitrophenyl ketone, C8H7NO3, crystallizes as a nearly planar molecule. Layers parallel to the (202) plane are stabilized by intermolecular C-H...O contacts. The molecular geometry is very similar to that of para-nitroacetophenone, but some bond lengths of the aromatic ring are significantly different. The molecular geometry agrees well with a recent room-temperature structure determination.
- Bolte, Michael,Scholtyssik, Maria
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- Monomeric Octahedral Ruthenium(II) Complex Enabled meta-C-H Nitration of Arenes with Removable Auxiliaries
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A removable oxime-assisted meta-C-H nitration of arenes is reported. Mechanistic investigations and DFT calculations reveal a new monomeric octahedral ruthenium(II) complex is responsible for the meta-selective nitration. Dioxygen as a cooxidant is crucial for achieving high conversion and good yields. Moreover, the utility of the present reaction protocol is further showcased by the late-stage modification of the clinical CNS drugs Diazepam and Fluvoxamine.
- Fan, Zhoulong,Li, Jie,Lu, Heng,Wang, Dong-Yu,Wang, Chao,Uchiyama, Masanobu,Zhang, Ao
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- A Stable Polyoxometalate-Based Metal-Organic Framework as Highly Efficient Heterogeneous Catalyst for Oxidation of Alcohols
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A novel copper-containing 3D polyoxometalate-based metal-organic framework (POMOF), H[Cu5ICuII(pzc)2(pz)4.5{P2W18O62}]·6H2O (HENU-1, HENU = Henan University; Hpzc = pyrazine-2-carboxylic acid, pz = pyrazine), was successfully isolated by a one-step hydrothermal method. In this compound, the {P2W18} polyanion acts as a seven-connected linker bridging adjacent 2D double-layer networks, as well as a template to induce the formation of the desired 3D framework. Particularly, the pz ligands are generated from pzc ligands in situ during the reaction process. HENU-1 exhibits not only good stability in air but also tolerance to acidic and basic media. It was first employed as a highly efficient heterogeneous catalyst for the oxidation of 1-phenylethanol into acetophenone, which shows 97% yield using tert-butyl hydroperoxide as oxidant with a turnover frequency of up to 9690·h-1, and was reused for at least five cycles without significant catalytic activity loss. No POM leaching or framework decomposition was observed in our study.
- Li, Dandan,Xu, Qiaofei,Li, Yingguang,Qiu, Yueting,Ma, Pengtao,Niu, Jingyang,Wang, Jingping
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- Aerobic oxidation of alcohols by using a completely metal-free catalytic system
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A metal-free reaction system of air, NH4NO3(cat), 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)(cat), and H +(cat) is introduced as a simple, safe, inexpensive, efficient and chemoselective mediator for aerobic oxidation of various primary and secondary benzyl and alkyl alcohols, including those bearing oxidizable heteroatoms (N, S, O) to the corresponding aldehydes or ketones. Air oxygen under slight overpressure plays the role of the terminal oxidant, which is catalytically activated by redox cycles of nitrogen oxides released from a catalytic amount of NH4NO3 and cocatalyzed by TEMPO (nitroxyl radical compound), under acidic conditions, which are essential for an overall activation of the reaction system. The synthetic value of this reaction system and its green chemical profile was illustrated by a 10 g scale-up experiment, performed in an open-air system by using a renewable and reusable polymer-supported form of TEMPO (OXYNITROXS100). The reaction solvent was recovered by distillation under atmospheric pressure, and the pure final product was isolated under reduced pressure; the acid activators (HCl or H 2SO4) were recovered as ammonium salts. A metal-free reaction system of air/NH4NO3(cat)/TEMPO (cat)/H+(cat) is introduced as a simple, safe, inexpensive, efficient and chemoselective mediator for aerobic oxidation of various primary and secondary benzyl, alkyl and allyl alcohols, including those bearing oxidizable heteroatoms (N, S, O) to the corresponding aldehydes or ketones. Copyright
- Prebil, Rok,Stavber, Gaj,Stavber, Stojan
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- Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation
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A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.
- Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei
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p. 5905 - 5908
(2021/06/18)
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- Preparation method of m-aminophenylacetylene
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The invention discloses a preparation method of m-aminophenylacetylene, belonging to the technical field of organic synthesis. The method comprises the following steps of: subjecting m-nitroacetophenone serving as a raw material to reacting with triethyl phosphite under the action of a catalyst, continuously converting the m-nitroacetophenone into enol form, and condensing the enol form with the triethyl phosphite to obtain condensation ester, wherein the condensation ester is easy to separate and high in purity, m-nitrophenylacetylene is generated from the ester under the action of strong base, and m-aminophenylacetylene is generated from the ester through reduction. Compared with an acetophenone chlorination method, the method of the invention has the advantages that phosphorus oxychloride does not need to be used for changing oxygen of the m-nitroacetophenone into chlorine, pollution is small, purity is high ( 98% or more), the use of high-pollution raw material reagents is avoided, operation is simple, the environment-friendly effects are realized, and industrial production can be conveniently realized.
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Paragraph 0008
(2021/05/29)
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- Interfacially synthesized 2D COF thin film photocatalyst: efficient photocatalyst for solar formic acid production from CO2and fine chemical synthesis
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The targeted synthesis of an efficient, visible light active, recyclable, freestanding covalent organic framework thin film photocatalyst for multi-faceted photocatalysis is the essence of the proposed work. A simple, scalable, reagent free synthesis of a thin film at the interface of 5,10,15,20-tetra-(4-aminophenyl)porphyrin, 2-vinylbenzene-1,4-dicarbaldehyde in nitrobenzene and aqueous glyoxal affords centimetre sized continuous 2D thin film with substantial stability, flexibility and efficient visible light activity. Strikingly different from the regular imine based COF, the incorporation of the glyoxal unit as a modulator helps in band gap tuning and induces flexibility within the thin film. An interplay between time and concentration helps in achieving a thin film photocatalyst with efficient photocatalytic activity for 1,4-NADH regeneration and selective formic acid formation from CO2. The optimum band edge position of the thin film photocatalyst also enables solar fine chemical synthesisviareductive dehalogenation under visible light illumination with excellent recyclability. The present work gives insight into visible light active thin film formation en route to metal-free sustainable photocatalysis.
- Yadav, Dolly,Kumar, Abhishek,Kim, Jae Young,Park, No-Joong,Baeg, Jin-Ook
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supporting information
p. 9573 - 9580
(2021/04/26)
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- The dehydrogenative oxidation of aryl methanols using an oxygen bridged [Cu-O-Se] bimetallic catalyst
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Herein, we report a new protocol for the dehydrogenative oxidation of aryl methanols using the cheap and commercially available catalyst CuSeO3·2H2O. Oxygen-bridged [Cu-O-Se] bimetallic catalysts are not only less expensive than other catalysts used for the dehydrogenative oxidation of aryl alcohols, but they are also effective under mild conditions and at low concentrations. The title reaction proceeds with a variety of aromatic and heteroaromatic methanol examples, obtaining the corresponding carbonyls in high yields. This is the first example using an oxygen-bridged copper-based bimetallic catalyst [Cu-O-Se] for dehydrogenative benzylic oxidation. Computational DFT studies reveal simultaneous H-transfer and Cu-O bond breaking, with a transition-state barrier height of 29.3 kcal mol?1
- Choudhury, Prabhupada,Behera, Pradyota Kumar,Bisoyi, Tanmayee,Sahu, Santosh Kumar,Sahu, Rashmi Ranjan,Prusty, Smruti Ranjita,Stitgen, Abigail,Scanlon, Joseph,Kar, Manoranjan,Rout, Laxmidhar
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supporting information
p. 5775 - 5779
(2021/04/12)
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- g-C3N4/H3PW4Mo8O40 S-scheme photocatalyst with enhanced photocatalytic oxidation of alcohols and sulfides
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In this work, graphitic carbon nitride (g-C3N4) decorated with molybdenum-substituted tungstophosphoric acid as a novel photocatalyst (H3PW4Mo8O40/g-C3N4) was used to catalyze the oxidation of alcohols and sulfides. H3PW4Mo8O40/g-C3N4 (PW4Mo8/g-C3N4) displays higher photocatalytic activity under visible light irradiation for the oxidation of alcohols and sulfides compared with Keggin/g-C3N4 (PW12/g-C3N4). To obtain the optimum value, molybdenum substitution contents (H3PW12-xMoxO40) were changed from x = 4 to 12. The results showed that PW4Mo8 produces the best yield under visible-light irradiation. The results showed that PW4Mo8 was the best sample. The reaction rate increase can be due to the redox and acid properties of PW4Mo8/g-C3N4. This study provides a new insight for the preparation of highly efficient photocatalysts for the oxidation of organic compounds.
- Fazlali, Farnaz,Khazaee, Zeynab,Najminejad, Zohreh,Nejat, Razieh,Shahraki, Somaye
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- Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4nanoparticles
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Visible light-mediated selective and efficient oxidation of various primary/secondary benzyl alcohols to aldehydes/ketones and oxidative dehydrogenation (ODH) of partially saturated heterocycles using a scalable and reusable heterogeneous photoredox catalyst in aqueous medium are described. A systematic study led to a selective synthesis of aldehydes under an argon atmosphere while the ODH of partially saturated heterocycles under an oxygen atmosphere resulted in very good to excellent yields. The methodology is atom economical and exhibits excellent tolerance towards various functional groups, and broad substrate scope. Furthermore, a one-pot procedure was developed for the sequential oxidation of benzyl alcohols and heteroaryl carbinols followed by the Pictet-Spengler cyclization and then aromatization to obtain the β-carbolines in high isolated yields. This methodology was found to be suitable for scale up and reusability. To the best of our knowledge, this is the first report on the oxidation of structurally diverse aryl carbinols and ODH of partially saturated N-heterocycles using a recyclable and heterogeneous photoredox catalyst under environmentally friendly conditions.
- Abinaya, R.,Balasubramaniam, K. K.,Baskar, B.,Divya, P.,Mani Rahulan, K.,Rahman, Abdul,Sridhar, R.,Srinath, S.
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p. 5990 - 6007
(2021/08/24)
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- Ru(iii) -based polyoxometalate tetramers as highly efficient heterogeneous catalysts for alcohol oxidation reactions at room temperature
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A novel ruthenium-containing polyoxometalate-based organic-inorganic hybrid, K4Na9H7.4[(AsW9O33)4(WO2)4{Ru3.2(C3H3N2)2}]·42H2O (1), was successfully synthesized by a one-step hydrothermal method under acidic conditions, which applied a self-assembly strategy between inorganic polyoxometalate based on trivacant [B-α-AsW9O33]9?{AsW9} fragments and an organic ligand, imidazole (C3H4N2). Compound1was further characterized by single-crystal X-ray diffraction, PXRD, IR spectroscopy, UV-Vis spectroscopy, ESI-MS, elemental analysis and TGA. Single-crystal X-ray diffraction data reveal that the polyanion consists of four trivacant Keggin-type polyanion {AsW9} building blocks bridged by four {WO6} units, leading to a crown-shaped tetrameric structure [(AsW9O33)4(WO2)4{Ru3.2(C3H3N2)2}]20.4?. The ESI-MS result reveals that the polyanion unit has excellent structural integrity in water. Moreover, the catalysis study of1was also further investigated, and the experimental results indicate heterogeneous catalyst1presents high efficiency (yield = 98%), excellent selectivity (>99%), and good recyclability for the oxidation of 1-(4-chlorophenyl)ethanol to 4′-chloroacetophenone with commercially available 70% aqueoustert-butyl hydroperoxide {TBHP (aq.)} as the oxidant at room temperature.
- Li, Huafeng,Ma, Pengtao,Niu, Jingyang,Song, Junpeng,Wang, Jingping,Wang, Yaqiong,Zhao, Xue,Zou, Yan
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p. 12664 - 12673
(2021/09/28)
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- Catalyst- and acid-free Markovnikov hydration of alkynes in a sustainable H2O/ethyl lactate system
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An efficient and sustainable protocol for the hydration of alkynes has been developed under metal/acid/catalyst/ligand-free conditions in a water/ethyl lactate mixture. The hydrogen-bond network in the ethyl lactate and water mixture plays a crucial and decisive role in activating the alkynes for hydration to afford the corresponding methyl ketones. This strategy gives the Markovnikov (ketone) addition product selectively over other possible products. The essential role of hydrogen bonding has been confirmed by experimental and theoretical techniques. A probable mechanism has been suggested by various control tests. The efficacy of the method has been further explored for the competent production of value-added α,β-unsaturated carbonyl compounds through the reaction of aldehydes with alkynes as ketonic surrogates. The environmentally benign hydration method takes place under mild conditions, has broad functional-group compatibility, and uses the ethyl lactate/water (1:3) medium as a “green alternative” in the absence of any hazardous, harmful, or expensive substances.
- Dandia, Anshu,Saini, Pratibha,Chithra,Vennapusa, Sivaranjana Reddy,Parewa, Vijay
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- MnO2as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins
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Efficient and mild reaction conditions for Wacker-type oxidation of terminal olefins of less explored homoallyl alcohols to β-hydroxy-methyl ketones have been developed by using a Pd(ii) catalyst and MnO2 as a co-oxidant. The method involves mild reaction conditions and shows good functional group compatibility along with high regio- and chemoselectivity. While our earlier system of PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is demonstrated.
- Fernandes, Rodney A.,Ramakrishna, Gujjula V.,Bethi, Venkati
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p. 6115 - 6125
(2020/10/27)
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- Visible light photoredox catalyzed deprotection of 1,3-oxathiolanes
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An efficient visible light photoredox catalyzed aerobic deprotection of 1,3-oxathiolanes using organic dye Eosin Y as a photocatalyst is disclosed. The deprotection procedure features the use of a metal-free catalyst, mild conditions, a broad range of substrate scope, and good functional group tolerance. 35 examples were tested under the standard conditions and most of them afforded the deprotected products in modest to high yields.
- Yang, Mingyang,Xing, Zhimin,Fang, Bowen,Xie, Xingang,She, Xuegong
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supporting information
p. 288 - 291
(2020/01/13)
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- Metal-Organic Framework Based on Heptanuclear Cu-O Clusters and Its Application as a Recyclable Photocatalyst for Stepwise Selective Catalysis
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Visible-light driven photoreactions using metal-organic frameworks (MOFs) as catalysts are promising with regard to their environmental friendly features such as the use of renewable and sustainable energy of visible light and potential catalyst recyclability. To develop potential heterogeneous photocatalysts, a family of three copper(II) coordination polymers bearing different Cu-O assemblies have been synthesized with the ligand 4,4-disulfo-[1,1-biphenyl]-2,2-dicarboxylate acid (H4DSDC), namely, {[Cu7(DSDC)2(OH)6(H2O)10]·xH2O}n (1), {[Cu4(DSDC)(4,4-bpy)2(OH)4]·2H2O}n (2), and {Cu2(DSDC)(phen)2(H2O)2}n (3) (4,4-bpy = 4,4-bipyridine and phen = 1,10-phenanthroline). Complex 1 represents a metal-organic framework featuring a NbO type topology constructed from the infinite linkage of heptanuclear [Cu7(μ3-OH)6(H2O)10]8+ clusters by deprotonated DSDC4- ligands, comprising one-dimensional hexagonal channels of a diameter around 11 ? that are filled with water molecules. The infinite waving {[Cu2(OH)2]2+}n ladderlike chains in complex 2 are bridged by DSDC4- and 4,4-bpy ligands into a three-dimensional framework. A two-dimensional layered structure is formed in complex 3 due to the existence of terminal phenanthroline ligands. All of the coordination polymers 1-3 are able to catalyze the visible-light driven oxidation of alcohols at mild conditions using hydrogen peroxide as an oxidant, in which complex 1 demonstrates satisfactory efficiency. Significantly for this photoreaction catalyzed by 1, the extent of oxidation over aryl primary alcohols is fully controllable with time-resolved product selectivity, giving either corresponding aldehydes or carboxylate acids in good yields. It is also remarkable that the photocatalyst could be recovered almost quantitatively on completion of the catalytic cycle without any structure change, and could be recycled for catalytic use for at least five cycles with constant efficiency. This photocatalyst with time-resolved selectivity for different products may provide new insight into the design and development of novel catalytic systems.
- Zhou, Jie,Huang-Fu, Xu,Huang, Yang-Ying,Cao, Chu-Ning,Han, Jie,Zhao, Xiao-Li,Chen, Xu-Dong
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p. 254 - 263
(2019/12/04)
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- Visible-light assisted of nano Ni/g-C3N4 with efficient photocatalytic activity and stability for selective aerobic C?H activation and epoxidation
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A selective, economical, and ecological protocol has been described for the oxidation of methyl arenes and their analogs to the corresponding carbonyl compounds and epoxidation reactions of alkenes with molecular oxygen (O2) or air as a green oxygen source, under mild reaction conditions. The nano Ni/g-C3N4 exhibited high photocatalytic activity, stability, and selectivity in the C?H activation of methyl arenes, methylene arenes, and epoxidation of various alkenes under visible- light irradiation without the use of an oxidizing agent and under base free conditions.
- Akrami, Zahra,Hosseini-Sarvari, Mona
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supporting information
(2020/10/13)
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- Catalytic oxidation of alcohols and alkyl benzenes to carbonyls using Fe3O4?SiO2?(TEMPO)-: Co -(Chlorophyll-CoIII) as a bi-functional, self-co-oxidant nanocatalyst
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Chlorophyll b was extracted from heliotropium europaeum plant, demetalated, allylated and grafted to acrylated TEMPO through a copolymerization protocol. Then, the chlorophyll monomers were coordinated to Co ions, immobilized on magnetic nanoparticles and the resulting hybrid was used as a powerful catalyst for a variety of oxidation reactions. By using the present method, oxidation of benzylic alcohols and alkyl benzenes to carbonyls was accomplished in water under aerobic conditions. Moreover, direct oxidation of alcohols to carboxylic acids was performed by adding NaOCl to the mixture. All entries were oxidized to the corresponding desired product with high to excellent yields and up to 97% selectivity. The catalyst was thoroughly characterized by CV, TGA, VSM, XRD, XPS, DLS, FE-SEM, TEM, UV-Vis, EDX, and BET analyses. The activity of the catalyst was investigated by applying various components of the catalyst to the oxidation model separately. The reasonable mechanisms are suggested based on the cooperation between the TEMPO groups and cobalt(iii) (or Co(iv)) sites on the catalyst. The catalyst could be recovered and reused for at least 7 consecutive recycles without any considerable reactivity loss. This journal is
- Hamah-Ameen, Baram Ahmed,Kazemnejadi, Milad,Mahmoudi, Boshra,Rostami, Amin
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p. 6600 - 6613
(2020/11/16)
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- Visible-light-driven photochemical activity of ternary Ag/AgBr/TiO2nanotubes for oxidation C(sp3)-H and C(sp2)-H bonds
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The Ag/AgBr/TiO2 ternary component nanotube as a heterogeneous photocatalyst was used for the solvent-free oxidation of the benzylic C(sp3)-H bond to the corresponding carbonyl compound or the solvent-controlled selective oxidative cleavage of the CC double bond of styrene to benzaldehyde under visible light at room temperature. A wide variety of carbonyl compounds were successfully synthesized through the developed photocatalytic process. Several advantages such as solvent-free conditions, sans additional oxidant, simple reaction, short reaction time, and easy separation of the product promote the reaction to be green. Moreover, the Ag/AgBr/TiO2 nanotubes could be used several times without reduction in their photocatalytic activity. This journal is
- Hosseini-Sarvari, Mona,Dehghani, Abdulhamid
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p. 16776 - 16785
(2020/10/27)
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- Preparation method of nitroacetophenone
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The invention discloses a preparation method of nitroacetophenone. The preparation method comprises the following step: by adopting nitrobenzoic acid as a material, carrying out three-step reaction ofacylating chlorination, condensation and hydrolysis to obtain a target product. The preparation method disclosed by the invention has the advantages that the reaction condition is mild, the aftertreatment is simple, and the problem of severe conditions of nitrating and oxidizing reactions in the traditional method is avoided; simultaneously, the preparation method has the advantages of less pollution and high yield and the like.
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Paragraph 0027
(2019/02/04)
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- Visible-Light-Driven Direct Oxidative Coupling Reaction Leading to Alkyl Aryl Ketones, Catalyzed by Nano Pd/ZnO
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Direct alkyl sp3 C–H activation to form new C–C bonds is one of the major challenges in synthetic chemistry. Herein, for the first time, we represent a new method, using nano Pd/ZnO which plays both as photoredox and transition-metal catalyst, for C–C bond formations. By using this catalyst, we have accomplished an oxidative coupling reaction between aryl halides and tertiary amines to yield the corresponding naturally occurring alkyl aryl ketones by using visible light irradiation. Furthermore, the carbonylation process was carried out on a 10 gram scale, with visible light and thermal condition, and it was proved to be scalable, efficient, and economical.
- Bazyar, Zahra,Hosseini-Sarvari, Mona
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supporting information
p. 2282 - 2288
(2019/04/03)
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- Pyrazine dicarboxylate-bridged arsenotungstate: Synthesis, characterization, and catalytic activities in epoxidation of olefins and oxidation of alcohols
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A praseodymium(iii)-containing arsenotungstate K16H15Li7[Pr2(H2O)3(pzdc)As3W29O103]2·38H2O (1) (pzdc = pyrazine-2,3-dicarboxylic acid) was synthesized by a conventional aqueous solution method and characterized by elemental analysis, IR spectroscopy, thermogravimetric analysis (TGA), powder X-ray diffraction (PXRD), and single crystal X-ray diffraction. Structural analysis revealed that compound 1 was constructed by two identical subunits {Pr2(H2O)3(AsW9O33)3W2O4} bridged together by two pzdc ligands. In addition, compound 1 could act as an efficient catalyst for the epoxidation of olefins and oxidation of alcohols with hydrogen peroxide (H2O2) as the oxidant. In particular, the turnover frequency (TOF) in the oxidation of 1-phenylethanol reached up to 10170 h-1, which is higher than that of previously reported catalysts.
- Ma, Xinyi,He, Peipei,Xu, Baijie,Lu, Jingkun,Wan, Rong,Wu, Hechen,Wang, Yuan,Ma, Pengtao,Niu, Jingyang,Wang, Jingping
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p. 12956 - 12963
(2019/09/07)
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- The synthesis of methyl triazole-4-carboxylate gold(I) complex and application on allene synthesis and alkyne hydration
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The methyl 1H-1,2,3-triazole-4-carboxylate containing a strong electron-withdrawing group was developed and applied as a ligand for gold(I) cations. The resulting ester-triazole gold(I) complex was investigated for its efficiency in catalyzing allene synthesis and alkyne hydration, in which an excellent catalytic efficiency was observed with low catalyst loadings.
- Hu, Wenkang,Shan, Liang,Ma, Fudong,Zhang, Yilin,Yang, Yongchun,Wang, Dawei
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- Pd(II)-Catalyzed Denitrogenative and Desulfinative Addition of Arylsulfonyl Hydrazides with Nitriles
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A Pd(II)-catalyzed denitrogenative and desulfinative addition of arylsulfonyl hydrazides with nitriles has been successfully achieved under mild conditions. This transformation is a new method for the addition reaction to nitriles with arylsulfonyl hydrazides as arylating agent, thus providing an alternative synthesis of aryl ketones. The reported addition reaction is tolerant to many common functional groups, and works well in the presence of electron-donating and electron-withdrawing substituents. Notably, the reported denitrogenative and desulfinative addition was also appropriate for alkyl nitriles, making this newly developed transformation attractive.
- Meng, Mengting,Yang, Liangfeng,Cheng, Kai,Qi, Chenze
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p. 3275 - 3284
(2018/03/25)
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- Nickel-Catalyzed Addition of Arylboronic Acids to Alkyl Nitriles for Synthesis of Aryl Ketones in Fluorinated Solvent
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A mild and efficient nickel-catalyzed addition of arylboronic acids to alkyl nitriles in a fluorinated solvent for the synthesis of various aryl ketones is described. A broad range of arylboronic acids and alkyl nitriles were investigated, and the desired products were obtained with good to excellent yields under the optimized conditions. This method provides an opportunity for the synthesis of aryl ketones from alkyl nitriles, especially acetonitrile, with a non-noble metal catalyst in one pot.
- Tu, Dong-Huai,Li, Yang,Zhao, Bo,Gu, Yu-Jie,Wang, Bo,Lu, Ju-You,Lu, Jian
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supporting information
p. 593 - 596
(2017/12/06)
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- Conversion of Olefins into Ketones by an Iron-Catalyzed Wacker-type Oxidation Using Oxygen as the Sole Oxidant
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We describe a mild and operationally simple procedure for the oxidation of olefins into ketones. The reaction is catalyzed by the hexadecafluorinated iron–phthalocyanine complex FePcF16 with stoichiometric amounts of triethylsilane as an additive under oxygen atmosphere to give ketones in good to high yields with excellent chemoselectivity and functional group tolerance. Ketone formation proceeds in up to 95 % yield and with 100 % regioselectivity while the corresponding alcohols were observed as side products.
- Puls, Florian,Kn?lker, Hans-Joachim
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supporting information
p. 1222 - 1226
(2018/01/01)
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- Preparation method of aromatic ketone
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The invention discloses a preparation method of aromatic ketone. Under the effects of a palladium catalyst and a nitrogen-containing ligand, nitrile compounds and arylsulfonylhydrazide take desulfurization addition reaction in an organic solvent; after the reaction is completed, post treatment is performed to obtain aromatic ketone. The reaction is applicable to aromatic nitrile compounds, and isalso applicable to aliphatic nitrile compounds; the reaction realizes the wide substrate applicability and functional group tolerance; the potential application value is realized in the aspect of aryl-carbonyl building.
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Paragraph 0056; 0057; 0058; 0060
(2018/09/11)
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- Design and Synthesis of Zirconium-Containing Coordination Polymer Based on Unsymmetric Indolyl Dicarboxylic Acid and Catalytic Application on Borrowing Hydrogen Reaction
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Catalytic borrowing hydrogen reaction is a very attractive transformation in the field of C-alkylation reaction. In this work, a new Zr (Zirconium)-containing coordination polymer containing unsymmetric indolyl dicarboxylic acid 1-(carboxymethyl)-1H-indole-5-carboxylic acid (H2CIA) was synthesized by the way of a solvothermal synthetic route and characterized by powder X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), Nitrogen adsorption-desorption, fourier transform infrared spectroscopy and X-ray photoelectronic spectroscopy (XPS). The coordination polymer Zr-CIA was employed as the catalyst for C-alkylation of acetophenone derivatives in the presence of benzyl alcohol. In addition, Zr-CIA catalyst was also observed to be effective in the reaction of alcohols with alcohols and high yields of alkylation products were achieved. Mechanism investigations were also conducted to better understand the catalysts and transformations. Meanwhile, the Zr-CIA could be reused at least five times without a notable decrease in activity and selectivity. (Figure presented.).
- Hu, Xinyu,Zhu, Haiyan,Sang, Xinxin,Wang, Dawei
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supporting information
p. 4293 - 4300
(2018/10/02)
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- A acetophenone compound of preparation method
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The invention relates to the technical field of organic synthesis and discloses an acetophenone compound preparation method. The acetophenone compound preparation method solves the problem that the traditional acetophenone preparation method has harsh reaction conditions, has complex processes, utilizes strong acid or heavy metal catalysis and pollutes the environment. The acetophenone compound preparation method comprises that an ethylbenzene compound, a copper catalyst, an oxidizing agent and a solvent are mixed, are put into a pressure-resistant pipe and undergo a reaction at a temperature of 0-50 DEG C for 2-12h, and the reaction product is separated so that the acetophenone compound is obtained. The acetophenone compound preparation method has the advantages of simple raw materials, simple operation and mild conditions.
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Paragraph 0077; 0078; 0079
(2018/05/24)
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- A synthesis method of erlotinib hydrochloride (by machine translation)
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The invention relates to a technical field of drug synthesis, relates to a new synthetic method of erlotinib hydrochloride. The steps are as follows: 1) to acetophenone as a starting material, in the nitration reaction takes place in the mixed between nitro acetophenone; 2) between nitro acetophenone with chlorinated reagent in the organic solvent in the reaction of chloride 1 - chloro - 1 - (3 - nitrophenyl) ethylene; 3) 1 - chloro - 1 - (3 - nitrophenyl) ethylene in the presence of an organic solvent and alkali to obtain between the dehydrochlorination nitrobenzene acetylene; 4) m acetylene through the nitro-selective reduction to obtain between amino acetylene; reduction method as a reducing agent or catalytic hydrogenation reduction; 5) between amino acetylene and 4 - chloro - 6, 7 - b - (2 - methoxyethoxy) quinazoline in reaction of organic solvent to obtain the erlotinib hydrochloride; raw materials of the invention is cheap, low production cost, simple operation, mild reaction conditions and the like, and is suitable for industrial production. (by machine translation)
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Paragraph 0024; 0025; 0026; 0027; 0028; 0029
(2017/06/30)
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- Mechanism of Catalytic Oxidation of Styrenes with Hydrogen Peroxide in the Presence of Cationic Palladium(II) Complexes
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Kinetic studies, isotope labeling, and in situ high-resolution mass spectrometry are used to elucidate the mechanism for the catalytic oxidation of styrenes using aqueous hydrogen peroxide (H2O2) and the cationic palladium(II) compound, [(PBO)Pd(NCMe)2][OTf]2 (PBO = 2-(pyridin-2-yl)benzoxazole). Previous studies have shown that this reaction yields acetophenones with high selectivity. We find that H2O2 binds to Pd(II) followed by styrene binding to generate a Pd-alkylperoxide that liberates acetophenone by at least two competitive processes, one of which involves a palladium enolate intermediate that has not been previously observed in olefin oxidation reactions. We suggest that acetophenone is formed from the palladium enolate intermediate by protonation from H2O2. We replaced hydrogen peroxide with t-butyl hydroperoxide and found that, although the palladium enolate intermediate was observed, it was not on the major product-generating pathway, indicating that the form of the oxidant plays a key role in the reaction mechanism.
- Walker, Katherine L.,Dornan, Laura M.,Zare, Richard N.,Waymouth, Robert M.,Muldoon, Mark J.
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p. 12495 - 12503
(2017/09/23)
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- Cationic Palladium(II) Complexes for Catalytic Wacker-Type Oxidation of Styrenes to Ketones Using O2 as the Sole Oxidant
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A series of new cationic palladium(II) complexes were prepared and studied for their ability to catalyze the Wacker-type oxidation of styrenes to their corresponding acetophenones using O2 as the sole oxidant. Catalysts are active at room temperature and the study highlights the importance of solvent choice and the need for ligand development in improving catalyst performance.
- Chai, Hongxin,Cao, Qun,Dornan, Laura M.,Hughes, N. Louise,Brown, Clare L.,Nockemann, Peter,Li, Jiarong,Muldoon, Mark J.
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p. 5604 - 5608
(2017/12/26)
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- Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations
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The present work addresses the development of an eco-friendly and cost-efficient protocol for the oxidation of primary and secondary alcohols to the corresponding aldehydes and ketones by mechanical processing under air. Ball milling was shown to promote the quantitative conversion of a broad set of alcohols into carbonyl compounds with no trace of an over-oxidation to carboxylic acids. The mechanochemical reaction exhibited higher yields and rates than the classical, homogeneous, TEMPO-based oxidation.
- Porcheddu, Andrea,Colacino, Evelina,Cravotto, Giancarlo,Delogu, Francesco,De Luca, Lidia
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supporting information
p. 2049 - 2055
(2017/10/16)
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- Cobaloxime-catalyzed hydration of terminal alkynes without acidic promoters
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Cobaloxime (Co(dmgBF2)2·2H2O), an inexpensive first-row transition-metal complex, catalyzed hydration of terminal alkynes gave the corresponding methyl ketones in good to excellent yields under neutral conditions (additional protic acids and silver salts are not required). A wide range of functional groups, such as allyl ether, benzyl ethers, carboxylic esters, imides, amides, nitro, and halogens, were tolerated. The mild reaction conditions together with the inexpensive feature and easy availability of the catalyst well address the current challenges in the field of alkyne hydration.
- Hou, Shengtai,Yang, Hongjian,Cheng, Bin,Zhai, Hongbin,Li, Yun
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supporting information
p. 6926 - 6929
(2017/07/10)
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- The facile approach to fabricate gold nanoparticles and their application on the hydration and dehydrogenation reactions
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A mild and practical strategy to prepare gold nanoparticles was developed. This gold particles supported mesoporous silica was fabricated from AuPPh3Cl under mild conditions and characterized through transmission electron microscopy, energy dispersive X-ray, X-ray power diffraction and X-ray photoelectron spectrometry. Interestingly, it was observed that this gold nanoparticle was effective to the hydration of alkynes and dehydrogenation of alcohols. The catalytic system can tolerate a variety of functional groups to afford the corresponding products in good to excellent yields.
- Huang, Ronghui,Fu, Yong,Zeng, Wei,Zhang, Liang,Wang, Dawei
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- Preparation method of 2-bromo-3'-methoxyacotophenone
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The invention relates to a preparation method of a medical intermediate, in particular to a preparation method of 2-bromo-3'-methoxyacotophenone. According to the preparation method, the target product is prepared by taking acetophenone, dimethyl sulfate and a brominating agent as main raw materials through the steps of a nitration reaction, a reduction reaction, a diazotization reaction, a hydrolysis reaction, a methylation reaction, a bromination reaction and the like. The preparation method has the advantages that the yields of the reactions are all 80% or above, the purity of the obtained target product 2-bromo-3'-methoxyacotophenone can reach 99.2%, the cost is low, and the yield and the purity are high; in the preparation process, the reaction conditions are mild, operation is easy, little harm is generated to the environment, and the preparation method is suitable for large-scale production.
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Paragraph 0028; 0035; 0042
(2017/08/25)
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- A new method for synthesizing zaleplon (by machine translation)
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The present invention provides a new method for synthesizing zaleplon. In particular, the method of the invention takes the acetophenone as raw materials, make N-ethyl-N-[ 3 - (3- dimethyl amine -1-oxo-2-propenyl) phenyl] acetamide, with 3-amino-4-cyano pyrazole reaction, forming N-[ 3 - (3-cyano-pyrazolo [1,5-α] pyrimidin-7-yl) phenyl]-N-ethyl acetamide. The synthetic route of the present invention of fewer steps, after treatment is simple, low cost, suitable for industrial production. (by machine translation)
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Paragraph 0117; 0118; 0119
(2016/10/10)
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- Sodium Bromide-Catalyzed Oxidation of Secondary Benzylic Alcohols Using Aqueous Hydrogen Peroxide as Terminal Oxidant
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A halide salt, hydroperoxide and AcOH catalyst system was applied to the oxidation of secondary benzylic alcohols. This simple system can be applied to a variety of secondary benzylic alcohols and scaled up for gram-scale preparation. High secondary benzylic alcohol selectivity of the present method is demonstrated in hydroxyketone synthesis. Based on several experimental results, a catalytic cycle for our oxidation is proposed.
- Komagawa, Hiromi,Maejima, Yukako,Nagano, Takashi
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supporting information
p. 789 - 793
(2016/03/09)
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- Visible light mediated chemo-selective oxidation of benzylic alcohols
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A highly chemoselective visible light mediated strategy has been developed for oxidation of benzylic alcohols. The method circumvents the use of toxic metal catalysts, high energy light source, and operates at room temperature. Furthermore reaction is easily scalable to gram levels.
- Devari, Shekaraiah,Rizvi, Masood Ahmad,Shah, Bhahwal Ali
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supporting information
p. 3294 - 3297
(2016/07/11)
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- Method for producing nitroacetophenone
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The present invention relates to the field of chemical engineering, and discloses a method for producing nitroacetophenone. The method is as below: pumping nitro ethylbenzene and a catalyst into an oxidation reactor, vacuumizing, substituting by oxygen, introducing oxygen in the oxidation reactor, controlling the oxygen pressure and flow, stirring the materials in the reactor, heating the reactor by steam, ceasing the heating after the reaction begins, cooling, and controlling the reaction temperature at 130-140 DEG C; when the ketone content reaches 80-85%, pressurizing the oxidation reaction oil into an acid removal kettle by the residual pressure into in the oxidation reactor, stirring, adjusting the pH value, stirring again, allowing to stand, and layering; discharging a nitrobenzene sodium formate solution to a reservoir to be recover nitrobenzoic acid; and pressurizing the oxidation reaction oil to a crystallization reactor, refrigerating, cooling, crystallizing, centrifuging, conducting spinning filter, washing and drying to obtain the nitroacetophenone product. The method of the invention eliminates exhaust emission, and has the advantages of rapid response, short cycle, and high conversion and yield of product.
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Paragraph 0045; 0046
(2016/10/31)
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- Cationic palladium(II) complexes as catalysts for the oxidation of terminal olefins to methyl ketones using hydrogen peroxide
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Ligated Pd(II) complexes have been studied for the catalytic oxidation of terminal olefins to their corresponding methyl ketones. The method uses aqueous hydrogen peroxide as the terminal oxidant; a sustainable and readily accessible oxidant. The choice of ligand, counterion and solvent all have a significant effect on catalytic performance and we were able to develop systems which perform well for these challenging oxidations.
- Cao, Qun,Bailie, David S.,Fu, Runzhong,Muldoon, Mark J.
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supporting information
p. 2750 - 2757
(2015/05/27)
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- Palladium catalyzed decarboxylative acylation of arylboronic acid with ethyl cyanoacetate as a new acylating agent: Synthesis of alkyl aryl ketones
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Palladium catalyzed acylation of arylboronic acid containing various functional groups was performed efficiently by ethyl cyanoacetate/substituted ethyl cyanoacetate as the acylating agent in aqueous triflic acid medium. The alkyl aryl ketones were obtained in good to excellent yields, first by addition of arylboronic acid to the nitrile group of ethyl cyanoacetate and their derivatives, followed by in situ decarboxylation of the resulting β-ketoester.
- Yousuf, Md,Das, Tuluma,Adhikari, Susanta
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p. 8763 - 8770
(2015/11/10)
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- Tsuji-Wacker Oxidation of Terminal Olefins using a Palladium-Carbon Nanotube Nanohybrid
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Palladium nanoparticles supported on carbon nanotubes were used in the Tsuji-Wacker oxidation. The palladium-based nanohybrid was found to be very active in combination with cuprous chloride for the selective oxidation of terminal olefins into methyl ketones. The co-catalytic system operates under very mild and sustainable conditions (room temperature, atmospheric pressure, low catalyst loading), as opposed to previously reported catalysts, and can be recycled without any loss in activity. Give it a whack: Palladium nanoparticles supported on carbon nanotubes are used in combination with cuprous chloride for the selective Tsuji-Wacker oxidation of terminal olefins into methyl ketones. The co-catalytic system operates under very mild and sustainable conditions and can be recycled without any loss in activity.
- Donck, Simon,Gravel, Edmond,Shah, Nimesh,Jawale, Dhanaji V.,Doris, Eric,Namboothiri, Irishi N. N.
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p. 2318 - 2322
(2015/08/11)
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- Metal free visible light driven oxidation of alcohols to carbonyl derivatives using 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) as catalyst
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3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) catalyzed oxidation of alcohols to the corresponding carbonyl compounds under visible light irradiation is described. This reaction occurs smoothly at room temperature and shows good tolerance of functional groups. It provides an alternative approach for the synthesis of alkyl and aryl aldehydes and ketones.
- Samanta, Suvendu,Biswas, Papu
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p. 84328 - 84333
(2015/10/28)
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- Copper-catalyzed one-pot synthesis of α-ketoamides from 1-arylethanols
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A copper-catalyzed one-pot strategy for the synthesis of α-ketoamides from 1-arylethanols is described. This triple oxidation of 1-arylethanols involves alcohol oxidation, sp3 C-H oxidation, and oxidative amidation with amines. The protocol is highly efficient, delivering α-ketoamides in good to excellent yields.
- Sharma, Nidhi,Kotha, Surya Srinivas,Lahiri, Nabajit,Sekar, Govindasamy
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p. 726 - 736
(2015/04/14)
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- Chemoenzymatic Deracemization of Secondary Alcohols by using a TEMPO-Iodine-Alcohol Dehydrogenase System
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A deracemization system for secondary alcohols was established after the analysis of individual steps and their compatibility in one pot. The chemical oxidation and bioreduction occurred in a sequential manner to yield 1-arylethanols and lineal aliphatic alcohols with excellent conversions and enantiomeric excess values. The oxidation step was performed by using 2,2,6,6-tetramethylpiperidin-1-oxyl and iodine. This chemical process was extremely favored by sonication, which allowed quantitative formation of the corresponding ketone intermediates after just 1 h. Simple destruction of iodine in the same pot allowed sequential bioreduction of the ketones by using either Prelog or antiPrelog enzymes, which led to the preparation of the enantiopure alcohols in excellent yields. Just a sec: The one-pot deracemization of secondary alcohols involving oxidation with 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) and iodine followed by alcohol dehydrogenase (ADH)-catalyzed bioreduction is described. 1-Arylethanols and lineal aliphatic alcohols are obtained with excellent conversions and enantiomeric excess values. LBADH=alcohol dehydrogenase from Lactobacillus brevis.
- Méndez-Sánchez, Daniel,Mangas-Sánchez, Juan,Lavandera, Iván,Gotor, Vicente,Gotor-Fernández, Vicente
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p. 4016 - 4020
(2015/12/26)
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- Silver-containing microemulsion as a high-efficient and recyclable catalytic system for hydration of alkynes
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A silver-catalyzed highly efficient and regioselective synthesis of ketones from a wide range of alkynes is described. The reaction is dramatically accelerated by its performance in aqueous emulsion, which is self-assembled by the addition of silver perfluorooctanesulfonate (1) and perfluorooctanesulfonic acid (PFOS) to water. The reaction is conducted under convenient conditions with broad substrate scope, including a variety of aromatic and aliphatic terminal alkynes and internal alkynes. Furthermore, the air- and light-stable silver catalytic microemulsion can be reused for 4 times with minimal change in catalytic efficiency.
- Dong, Qizhi,Li, Ningbo,Qiu, Renhua,Wang, Jinying,Guo, Cancheng,Xu, Xinhua
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p. 122 - 127
(2015/10/12)
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- CONTINUOUS TWO STEP FLOW SYNTHESIS OF M-AMINO ACETOPHENONE
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Disclosed herein is a continuous tubular reactor based conversion of acetophenones to amino substituted acetophenones wherein the nitration is carried out at ?10 to 10° C. followed by reduction to m-nitrophenone resulting in uniform output of product, said process comprising the steps of: a) Nitrating acetophenone with nitrating agent (nitration mixture or fuming nitric acid) at ?10 to 10° C.; b) Isolating m-nitro acetophenone from a mixture of o and m-nitro acetophenone and c) Reducing the m-nitro to obtain m-amino acetophenone.
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Paragraph 0062-0068
(2014/09/03)
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- An efficient approach to deoximation using hexachlorodisilane under mild conditions
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A simple, facile, and efficient procedure for deoximation of oximes to the corresponding ketones and aldehydes with hexachlorodisilane (Si2Cl6) in the presence of SiO2 from good to high yields is described. Apparently, SiO2 greatly increases the reaction rate and product yield. The proposed procedure is more advantageous than those described previously due to its higher efficiency, milder reaction conditions, shorter reaction, and easier work-up.
- Du, Liyong,Gao, Jing,Yang, Shuyang,Wang, Dawei,Han, Xinxin,Xu, Yongjian,Ding, Yuqiang
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p. 2200 - 2204
(2015/02/02)
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- Heterocycle-substituted tetrazole ligands for copper-catalysed aerobic oxidation of alcohols
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An efficient copper-catalysed aerobic oxidation of alcohols has been established, which employed heterocycle-substituted tetrazoles as ligands. The commercially available (S)-5-(pyrrolidin-2-yl)-1H-tetrazole proved as the best ligand for this oxidation. Under optimized conditions, the substrate scope was broadened. A plausible mechanism was also proposed.
- Liu, Yangyang,Xie, Aming,Li, Junjian,Xu, Xiao,Dong, Wei,Wang, Boliang
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p. 9791 - 9796
(2015/01/09)
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- Solvent-free oxidation of secondary alcohols to carbonyl compounds by 1, 3-dibromo-5, 5-dimethylhydantoin (DBDMH) and 1, 3-dichloro-5, 5-dimethylhydantoin (DCDMH)
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Aldehydes and ketones are important intermediates, especially for the construction of carbon-skeletons. The oxidation of alcohols is so important that a large number of methods and reagents have been reported for this purpose. N-halo reagents are widely used in organic synthesis and as a continuation of our interest in the application of N-halo compounds in organic synthesis, dibromo dimethylhydantoin (DBDMH) and dichloro dimethylhydantoin (DCDMH) were used for the oxidation of alcohols and our ongoing work on development of highly efficient oxidation protocols. We observed the oxidation of secondary alcohols with stoichiometric amounts of DBDMH and DCDMH under solvent-free conditions in the range of temperature 70-80 °C.
- Khazaei, Ardeshir,Abbasi, Fatemeh,Kianiborazjani, Maryam,Saednia, Shahnaz
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p. 361 - 364
(2014/02/14)
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