- A very simple method to synthesize nano-sized manganese oxide: An efficient catalyst for water oxidation and epoxidation of olefins
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Nano-sized particles of manganese oxides have been prepared by a very simple and cheap process using a decomposing aqueous solution of manganese nitrate at 100 °C. Scanning electron microscopy, transmission electron microscopy and X-ray diffraction spectrometry have been used to characterize the phase and the morphology of the manganese oxide. The nano-sized manganese oxide shows efficient catalytic activity toward water oxidation and the epoxidation of olefins in the presence of cerium(iv) ammonium nitrate and hydrogen peroxide, respectively.
- Najafpour, Mohammad Mahdi,Rahimi, Fahimeh,Amini, Mojtaba,Nayeri, Sara,Bagherzadeh, Mojtaba
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- Enthalpy- and/or entropy-controlled asymmetric oxidation: Stereocontrolling factors in Mn-salen-catalyzed oxidation
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The degree of enantioselection by second-generation Mn-salen complexes was found to depend upon the conformation of their ligand and substrate nucleophilicity. Oxidation of usual olefins was better effected by using (R,S)-Mn-salen complexes as catalysts, while that of more nucleophilic ones was achieved by using (R,R)-Mn-salen complexes. This phenomenon was explained by analyzing the enthalpy and entropy factors of the reactions. (C) 2000 Elsevier Science Ltd.
- Nishida,Miyafuji,Ito,Katsuki
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- Biomimetic epoxidation of alkenes with sodium periodate catalyzed by tetraphenylporphyrinatomanganese(III) chloride supported on multiwall carbon nanotubes
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The biomimetic epoxidation of alkenes catalyzed by tetraphenylporphyrinatomanganese(III) chloride, [Mn(TPP)Cl], immobilized on multiwall carbon nanotubes modified with 4-aminopyridine and 4-aminophenol is reported. These heterogenized catalysts were used as efficient and reusable catalysts for epoxidation of a variety of cyclic and linear alkenes with sodium periodate under mild conditions. The catalysts, [Mn(TPP)Cl@amine-MWCNT], were characterized by physico-chemical and spectroscopic methods. The effect of ultrasonic irradiation on these catalytic systems was also investigated. The catalysts were reused several times without loss of their activity. Springer Science+Business Media B.V. 2011.
- Zakeri, Maryam,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Tangestaninejad, Shahram,Mirkhani, Valiollah,Khosropour, Ahmad Reza,Alizadeh, Mohammad
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- Mechanistic studies of olefin epoxidation by a manganese porphyrin and hypochlorite: An alternative explanation of "saturation kinetics"
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The catalytic epoxidation of olefins with Mn(TMP)Cl with phase-transfer catalysis and hypochlorite has been reexamined from the point of view of material balance and stability of this system in the presence of three axial ligands. The efficiency (yield of epoxide formation based on OCl- consumed) is found to fall off with decreasing olefin concentration and to be influenced by the nature of the axial base. With t-BuPy as the axial ligand, the stirred system in the absence of olefin is found to be stable over prolonged periods and does not lose OCl- titer. This leads to the conclusion that, in the presence of low olefin concentration, the missing OCl- equivalents must be consumed in a side reaction with the olefin. It is proposed that extensive byproduct oxidations account for loss of OCl-, low efficiency, and apparent "saturation kinetics" we previously reported.
- Collman, James P.,Brauman, John I.,Hampton, Philip D.,Tanaka, Hiroo,Bohle, D. Scott,Hembre, Robert T.
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- Chiral porous poly(ionic liquid)s: Facile one-pot, one-step synthesis and efficient heterogeneous catalysts for asymmetric epoxidation of olefins
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Ionic liquids are potential media/solvents for asymmetric synthesis when combined with chiral catalysts, while most reported catalysts are homogenous, making them difficult to separate from the reaction systems. Herein, chiral porous poly(ionic liquid)s (
- Tian, Yabing,Wang, Jixia,Zhang, Shiguo,Zhang, Yan
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- Dioxo-molybdenum(VI) unsymmetrical Schiff base complex supported on CoFe2O4@SiO2 nanoparticles as a new magnetically recoverable nanocatalyst for selective epoxidation of alkenes
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In the present work, a dioxo-molybdenum unsymmetrical Schiff base complex, [MoO2(salenac-OH)], in which salenac-OH = [9-(2',4'-dihydroxyphenyl)-5,8-diaza-4-methylnona-2,4,8-trienato](-2), has been prepared and covalently immobilized on the sili
- Ardakani, Mehdi Hatefi,Sabet, Mohammad,Samani, Mahnaz
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- Efficient and selective oxidation of hydrocarbons with tert-butyl hydroperoxide catalyzed by oxidovanadium(IV) unsymmetrical Schiff base complex supported on γ-Fe2O3 magnetic nanoparticles
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The catalytic activity of an oxidovanadium(IV) unsymmetrical Schiff base complex supported on γ-Fe2O3 magnetic nanoparticles, γ-Fe2O3@[VO(salenac-OH)] in which salenac-OH = [9-(2′,4′-dihydroxyphenyl)-5,8-diaza-4
- Samani, Mahnaz,Ardakani, Mehdi Hatefi,Sabet, Mohammad
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p. 1481 - 1494
(2022/01/22)
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- Enhanced enantioselectivity in heterogeneous manganese-catalyzed asymmetric epoxidation with nanosheets modified amino acid Schiff bases as ligands by modulating the orientation and the arrangement order
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Catalytic enantioselective epoxidation of olefins plays an important role in the production of optically-active epoxy. Transition-metal complexes prove efficient for the catalytic epoxidation of un-functionalized olefins by employing privileged chiral lig
- An, Zhe,Han, Hongbo,He, Jing,Jiang, Yitao,Ping, Qi,Shu, Xin,Song, Hongyan,Tang, Yuanzhong,Wang, Wenlong,Xiang, Xu,Zhu, Yanru
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- Modification of MnFe2O4 surface by Mo (VI) pyridylimine complex as an efficient nanocatalyst for (ep)oxidation of alkenes and sulfides
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In this current paper, we report a new type of heterogeneous molybdenum (+6) complex, prepared by covalent grafting of cis-dioxo?molybdenum (VI) pyridylimine complex on the surface of MnFe2O4 nanoparticles (NP) and characterized using various physicochemical techniques. The recyclable prepared nanocatalyst was tested for sulfoxidation of sulfides and epoxidation of alkenes under solvent-free condition. The catalyst exhibited high turnover frequency for the oxidization of cyclooctene and cyclohexene (10,850 h?1) and thioanisole and dimethyl sulfide (41,250 h?1). The synthesized catalyst was found highly efficient, retrievable and eco-friendly catalyst for the (ep)oxidation of alkenes and sulfides in excellent yields in a short time. Furthermore, the synthesized nanocatalyst can be reused for four runs without apparent loss of its catalytic activity in the oxidation reaction.
- Bouzari, Narges,Bezaatpour, Abolfazl,Babaei, Behnam,Amiri, Mandana,Boukherroub, Rabah,Szunerits, Sabine
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- Anchoring of a terpyridine-based Mo(VI) complex on manganese ferrite as a recoverable catalyst for epoxidation of olefins under solvent-free conditions
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A magnetically separable heterogeneous nanocatalyst was obtained by anchoring a terpyridine-based Mo(VI) complex on modified MnFe2O4 nanoparticles and characterized by Fourier transform infrared (FT-IR), X-ray diffraction (XRD) and diffuse reflectance spectroscopies (DRS), transmission electron microscopy (TEM), scanning electron microscopy (SEM), vibrating sample magnetometry (VSM), X-ray photoelectron spectroscopy (XPS) and Brunauer-Emmett-Teller (BET) analysis. The catalytic activity of the supported molybdenum based catalyst was evaluated in the selective epoxidation of various olefins (cyclooctene, limonene, 1-dodecane, 1-heptene, styrene, 1-indene, α-pinene, cyclohexene) with tert-butyl hydroperoxide (TBHP) as an oxidant under solvent-free conditions. This nanocatalyst was easily separated by using an external magnetic field and reused consecutively at least five times with no significant loss in selectivity and catalytic activity. The short reaction time, simple preparation, high conversion, good physicochemical stability and magnetic recycling of the catalysts are beneficial.
- Fadaei Sarabi, Mahsa,Bezaatpour, Abolfazl,Mahmoudi, Ali
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p. 1597 - 1612
(2021/03/29)
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- Liquid-phase oxidation of olefins with rare hydronium ion salt of dinuclear dioxido-vanadium(V) complexes and comparative catalytic studies with analogous copper complexes
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Homogeneous liquid-phase oxidation of a number of aromatic and aliphatic olefins was examined using dinuclear anionic vanadium dioxido complexes [(VO2)2(salLH)]? (1) and [(VO2)2(NsalLH)]? (2) and dinuclear copper complexes [(CuCl)2(salLH)]? (3) and [(CuCl)2(NsalLH)]? (4) (reaction of carbohydrazide with salicylaldehyde and 4-diethylamino salicylaldehyde afforded Schiff-base ligands [salLH4] and [NsalLH4], respectively). Anionic vanadium and copper complexes 1, 2, 3, and 4 were isolated in the form of their hydronium ion salt, which is rare. The molecular structure of the hydronium ion salt of anionic dinuclear vanadium dioxido complex [(VO2)2(salLH)]? (1) was established through single-crystal X-ray analysis. The chemical and structural properties were studied using Fourier transform infrared (FT-IR), ultraviolet–visible (UV–Vis), 1H and 13C nuclear magnetic resonance (NMR), electrospray ionization mass spectrometry (ESI-MS), electron paramagnetic resonance (EPR) spectroscopy, and thermogravimetric analysis (TGA). In the presence of hydrogen peroxide, both dinuclear vanadium dioxido complexes were applied for the oxidation of a series of aromatic and aliphatic alkenes. High catalytic activity and efficiency were achieved using catalysts 1 and 2 in the oxidation of olefins. Alkenes with electron-donating groups make the oxidation processes easy. Thus, in general, aromatic olefins show better substrate conversion in comparison to the aliphatic olefins. Under optimized reaction conditions, both copper catalysts 3 and 4 fail to compete with the activity shown by their vanadium counterparts. Irrespective of olefins, metal (vanadium or copper) complexes of the ligand [salLH4] (I) show better substrate conversion(%) compared with the metal complexes of the ligand [NsalLH4] (II).
- Maurya, Abhishek,Haldar, Chanchal
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- Asymmetric azidohydroxylation of styrene derivatives mediated by a biomimetic styrene monooxygenase enzymatic cascade
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Enantioenriched azido alcohols are precursors for valuable chiral aziridines and 1,2-amino alcohols, however their chiral substituted analogues are difficult to access. We established a cascade for the asymmetric azidohydroxylation of styrene derivatives leading to chiral substituted 1,2-azido alcohols via enzymatic asymmetric epoxidation, followed by regioselective azidolysis, affording the azido alcohols with up to two contiguous stereogenic centers. A newly isolated two-component flavoprotein styrene monooxygenase StyA proved to be highly selective for epoxidation with a nicotinamide coenzyme biomimetic as a practical reductant. Coupled with azide as a nucleophile for regioselective ring opening, this chemo-enzymatic cascade produced highly enantioenriched aromatic α-azido alcohols with up to >99% conversion. A bi-enzymatic counterpart with halohydrin dehalogenase-catalyzed azidolysis afforded the alternative β-azido alcohol isomers with up to 94% diastereomeric excess. We anticipate our biocatalytic cascade to be a starting point for more practical production of these chiral compounds with two-component flavoprotein monooxygenases.
- Franssen, Maurice C. R.,Hollmann, Frank,Martínez-Montero, Lía,Paul, Caroline E.,Süss, Philipp,Schallmey, Anett,Tischler, Dirk
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p. 5077 - 5085
(2021/08/16)
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- Immobilization of (tartrate-salen)Mn(III) polymer complexes into SBA-15 for catalytic asymmetric epoxidation of alkenes
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A series of (tartrate-salen)Mn(III) polymer complexes were prepared and immobilized into SBA-15, being subsequently employed as catalysts in the asymmetric epoxidation of alkenes. 1H NMR, FT-IR, UV–vis, elemental analysis, GPC and ICP-AES demonstrated the successful synthesis of polymer complexes, while powdered XRD, nitrogen physisorption and XPS studies proved the immobilization of polymer complexes into SBA-15. Both homogeneous and heterogeneous catalysis revealed that configurations of major epoxide products were still determined by salen chirality but e.e. values could be improved when tartrate and salen were configurationally identical. Combinations of (R,R)-salen with (R,R)-tartrate usually offered higher enantioselectivities. SBA-15 was satisfactory supporting material due to the high enantioselectivities and recycling yields obtained. The synthesized SBA-15-supported (tartrate-salen)Mn(III) catalysts showed continuous high enantioselectivities for epoxidation of α-methylstyrene, indicating great prospects for large-scale production.
- Jia, Yihong,ALOthman, Zeid A.,Liang, Rui,Cha, Shuangshuang,Li, Xiaoyong,Ouyang, Weiyi,Zheng, Aqun,Osman, Sameh M.,Luque, Rafael,Sun, Yang
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- Homogeneous catalytic oxidation of alkenes employing mononuclear vanadium complex with hydrogen peroxide
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Abstract: Homogeneous liquid-phase oxidation of alkenes (allylbenzene, cis-cyclooctene, 4-chlorostyrene, styrene, 2-norbornene, 1-methyl cyclohexene, indene, lemonine, and 1-hexene) were catalyzed by using vanadium complex [VO(hyap)(acac)2] in existence of H2O2. The complex [VO(hyap)(acac)2] was formed as a crystal by the reaction of [VO(acac)2] and 2-hydroxyacetophenone (hyap) in the presence of methanol by refluxing the reaction mixture. Various analytical and spectroscopic techniques, namely FTIR, ESI–MS, UV–Vis, single-crystal XRD, and EPR, were used to analyze and optimize the structure of the complexes. Graphic abstract: [Figure not available: see fulltext.].
- Maurya, Abhishek
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p. 3261 - 3269
(2020/07/14)
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- Asymmetric epoxidation of unfunctionalized olefins with C2-symmetrical diphenol-derived axially coordinated homogeneous chiral bi-Mn(III) salen complexes
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A novel type of C2-symmetrical diphenol-derived and axially coordinated homogeneous chiral bi-Mn(III) salen complexes are synthesized and their catalytic effects in asymmetric epoxidation of unfunctionalized olefins are investigated in details. The results show that excellent enantioselectivities and high activities are achieved (enantioselectivities up to >99% in 99.9%) in the absence of expensive NMO. Compared with Jacobsen's catalyst, the configuration of C2-symmetrical homogeneous chiral bi-Mn(III) salen complex contribute to the catalytic reactivity and stability. Furthermore, these new homogeneous catalysts could be easily recovered and reused for 5 cycles without significant loss of their properties.
- Dong, Tianyi,Wu, Xiaoju,Cai, Jiali,Huang, Jing
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- Visible-Light-Driven N-Heterocyclic Carbene Catalyzed γ- and ?-Alkylation with Alkyl Radicals
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The merging of photoredox catalysis and N-heterocyclic carbene (NHC) catalysis for γ- and ?-alkylation of enals with alkyl radicals was developed. The alkylation reaction of γ-oxidized enals with alkyl halides worked well for the synthesis γ-multisubstituted-α,β-unsaturated esters, including those with challenging vicinal all-carbon quaternary centers. The synthesis of ?-multisubstituted-α,β-γ,δ-diunsaturated esters by an unprecedented NHC-catalyzed ?-functionalization was also established.
- Dai, Lei,Xia, Zi-Hao,Gao, Yuan-Yuan,Gao, Zhong-Hua,Ye, Song
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supporting information
p. 18124 - 18130
(2019/11/13)
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- Computationally guided design of a readily assembled phosphite-thioether ligand for a broad range of pd-catalyzed asymmetric allylic substitutions
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A modular approach employing indene as common starting material, has enabled the straightforward preparation in three reaction steps of P-thioether ligands for the Pd-catalyzed asymmetric allylic substitution. The analysis of a starting library of P-thioether ligands based on rational design and theoretical calculations has led to the discovery of an optimized anthracenethiol derivative with excellent behavior in the reaction of choice. Improving most approaches reported to date, this ligand presents a broad substrate and nucleophile scope. Excellent enantioselectivities have been achieved for a range of linear and cyclic allylic substrates using a large number of C-, N-, and O-nucleophiles (40 compounds in total). The species responsible for the catalytic activity have been further investigated by NMR in order to clearly establish the origin of the enantioselectivity. The resulting products have been derivatized by means of ring-closing metathesis or Pauson-Khand reactions to further prove the synthetic versatility of the methodology for preparing enantiopure complex structures.
- Biosca, Maria,Margalef, Jèssica,Caldentey, Xisco,Besora, Maria,Rodríguez-Escrich, Carles,Saltó, Joan,Cambeiro, Xacobe C.,Maseras, Feliu,Pàmies, Oscar,Diéguez, Montserrat,Pericàs, Miquel A.
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p. 3587 - 3601
(2018/04/14)
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- Collaborative effect of Mn-porphyrin and mesoporous SBA-15 in the enantioselective epoxidation of olefins with oxygen
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The rational design of heterogeneous, low cost transition metal complexes that can catalyze olefin with high enantioselectivity and activity has been a challenging goal for the synthetic chemist. In this study a chiral ion pair strategy was used for the synthesis of a biomimetic efficient manganese-tetrapyridylporphyrin (H2TPyP) catalyst for the asymmetric epoxidation of olefins with O2. Complex Mn-TPyP was covalently linked to mesoporous SBA-15 in heme-type environments and its counter ion was replaced by L-tartrate anion (SBA15-[Mn(TPyP)TA]). Chiral and achiral homogeneous analogous of Mn-TPyP were also prepared. The Mn-porphyrin confined in nanoreactors of SBA-15 exhibited enhanced activity (TOF = 652 h?1) and enantiomeric excess (ee 93%) compared with the value obtained when the same chiral catalyst functioned in homogeneous solution (TOF 97 h?1 and ee 83%) in the oxidation of 1-decene with O2/isobutyraldehyde. The high specific surface area, uniformly sized pore channels and site isolated active centers of the catalyst may contribute to the high activity and enantioselectivity. SBA15-[Mn(TPyP)TA] was structurally stable and could be recycled for repeated use. Total turnover number in the oxidation of styrene after five cycles was 47,400 with 86% epoxide selectivity and ee 86%.
- Berijani, Kayhaneh,Hosseini-Monfared, Hassan
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p. 113 - 120
(2017/11/10)
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- Chiral Manganese Aminopyridine Complexes: the Versatile Catalysts of Chemo- and Stereoselective Oxidations with H2O2
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In the last decade, manganese(II) complexes with N-donor tetradentate aminopyridine ligands emerged as efficient catalysts of enantioselective epoxidation of olefins and direct selective oxidation of C?H groups in complex organic molecules, with environmentally benign oxidant hydrogen peroxide. In this personal account, we summarize the progress of these catalysts with regard to ligands design, structure-reactivity correlations, evaluation of the substrate scope, as well as mechanistic studies, shedding light on the nature of active sites and the mechanisms of selective oxygenations. Several practically promising catalytic syntheses with the aid of Mn aminopyridine catalysts are exemplified.
- Ottenbacher, Roman V.,Talsi, Evgenii P.,Bryliakov, Konstantin P.
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- Highly efficient asymmetric epoxidation of olefins with a chiral manganese-porphyrin covalently bound to mesoporous SBA-15: Support effect
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A chiral MnIII-porphyrin complex covalently bonded with mesoporous SBA-15 (SBA15-[Mn(TCPP-R?)Cl]) was synthesized and fully characterized. The heterogeneous SBA15-[Mn(TCPP-R?)Cl] exhibited remarkable catalytic activity toward enantioselective olefin epoxidation using O2 as terminal oxidant in the presence of isobutyraldehyde. The catalyst showed higher enantioselectivity than its homogeneous counterpart in the oxidation of α-methylstyrene. SBA15-[Mn(TCPP-R?)Cl] catalyzed epoxidation of styrene was achieved within 8?h and optically active styrene oxide was obtained in 89% ee and 90% yield. Likewise, styrene derivatives (trans-β-methylstyrene, indene), conjugated cis- and trans-disubstituted olefins (e.g. cis- and tans-stilbene) and terminal olefins were converted effectively to their corresponding epoxides in 63–99%?ee under the Mn(III)-catalyzed conditions. The catalyst could be recycled five times without any significant loss in activity.
- Farokhi, Afsaneh,Hosseini Monfared, Hassan
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p. 229 - 238
(2017/06/19)
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- Heterogeneous Jacobsen's catalyst on alkoxyl-modified zirconium poly (styrene-phenylvinylphosphonate)-phosphate (ZPS-PVPA) for asymmetric epoxidation
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Chiral Jacobsen's catalysts grafted onto alkoxyl-modified ZPS-PVPA exhibit excellent activities (conv%, up to 96; sele%, up to 96; ee%, up to >99) in the asymmetric epoxidations of unfunctionalized olefins. The superior stabilities and the comfortable dis
- Huang, Jing,Ding, Weigang,Cai, Jiali
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- Cu-Schiff base complex grafted onto graphene oxide nanocomposite: Synthesis, crystal structure, electrochemical properties and catalytic activity in oxidation of olefins
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Copper(II) Schiff base complex has been immobilized onto graphene oxide (GO) via covalent bonding. The nanocomposite was characterized using powder X-ray diffraction (XRD), Fourier transform infrared (FT-IR) and UV–visible spectroscopies, transmission electron microscopy (TEM), scanning electron microscopy (SEM), thermo-gravimetric analysis (TGA) and the energy-dispersive X-ray spectroscopy (EDX). The amount of catalyst loading on the solid support was determined by atomic absorption spectroscopy. The thermogravimetric analysis (TGA) demonstrated that the nanocatalyst was stable up to almost 220?°C, exhibiting high thermostability. Highly active and selective catalyst was found with excellent turnover numbers (up to 47,000 for oxidation of styrene) for the epoxidation of olefins in ethanol using aqueous hydrogen peroxide as oxidant. It could be readily reused for successive ten times without discernible activity and selectivity deterioration, which displays potential for practical applications.
- Rayati, Saeed,Khodaei, Elham,Shokoohi, Saeedeh,Jafarian, Majid,Elmi, Bahareh,Wojtczak, Andrzej
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p. 520 - 528
(2017/07/22)
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- Co(II) Schiff base complex decorated on polysalicylaldehyde as an efficient, selective, heterogeneous and reusable catalyst for epoxidation of olefins in mild and self-coreductant conditions
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Abstract: A new Co(II)-Schiff base complex was decorated on a polysalicylaldehyde (PSA) framework and used as a selective and efficient catalyst for the epoxidation of alkenes in the presence of O2 as a green source of oxygen without aco-reductant. The catalyst was characterized step by step by FTIR, UV–Vis, 1H NMR, TGA, CHN, XPS and EDX analyses. Loading an amount of Co ions in the catalyst as well as its leaching amount were studied by an ICP-OES instrument. The catalyst demonstrated excellent activity for the of a variety of alkenes in a mild, inexpensive and efficient protocol. Also, the catalyst can be simply recovered from the reaction mixture and reused for several times without any noteiceable loss in its activity. Reaction parameters including temperature, oxygen flow volume, catalyst amount and solvent were screened by reaction time. Catalytic studies including XPS spectroscopy and some blank experiments were performed to obtain an initial insight into the reaction mechanism. Also, the reactivity of the novel catalyst was evaluated as the turnover frequency. Graphical Abstract: A new and efficient protocol have been developed for the selective epoxidation of olefins using a heterogeneous recyclable Co(II)-Schiff base complex of polysalicylaldehyde in mild and self-coreductant conditions by molecular oxygen.
- Kazemnejadi, Milad,Shakeri, Alireza,Nikookar, Mahsa,Mohammadi, Mohammad,Esmaeilpour, Mohsen
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p. 6889 - 6910
(2017/10/05)
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- Aerobic Stereoselective Oxidation of Olefins on a Visible-Light-Irradiated Titanium Dioxide-Cobalt-Ascorbic Acid Nanohybrid
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A visible-light-driven photocatalytically active nanocrystalline TiO2 was prepared by surface modification with a cobalt-ascorbic acid complex. The photocatalyst exhibited high activity and excellent chemo-, diastereo-, and stereoselectivities
- Jafarpour, Maasoumeh,Feizpour, Fahimeh,Rezaeifard, Abdolreza
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supporting information
p. 235 - 238
(2017/01/25)
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- Epoxidation of alkenes by an oxidovanadium(IV) tetradentate Schiff base complex as an efficient catalyst with tert-butyl hydroperoxide
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A new asymmetrical tetradentate N2O2Schiff base ligand was synthesized from 2-hydroxyacetophenon, 2-hydroxynaphthaldehyde and 1,2 phenylenediimine. The new oxidovanadium(IV) Schiff base complex, VIVOL (L?=?N-2-hydroxyacetophenon-N′-2-hydroxynaphthaldehyde-1,2 phenylenediimine), was prepared by reaction of Schiff base ligand with vanadyl acetylacetonate. The Schiff base ligand (L) and the oxidovanadium(IV) complex were characterized by spectroscopic methods. The crystal structure of the complex was determined by the single crystal X-ray analysis. The complex crystallized in the orthorhombic system, having one V4+ion coordinating in an approximately square pyramidal N2O3geometry by two azomethine N atoms and phenolic oxygens from Schiff base ligand in a square plane and one oxygen atom in an apical position. Electrochemical properties of the complex were examined by means of cyclic voltammetry. The catalytic activity of the oxidovanadium(IV) Schiff base complex was tested in the epoxidation of cyclooctene.
- Sedighipoor, Maryam,Kianfar, Ali Hossein,Mahmood, Wan Ahmad Kamil,Azarian, Mohammad Hossein
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p. 116 - 121
(2016/12/27)
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- The Activation of Carboxylic Acids via Self-Assembly Asymmetric Organocatalysis: A Combined Experimental and Computational Investigation
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The heterodimerizing self-assembly between a phosphoric acid catalyst and a carboxylic acid has recently been established as a new activation mode in Br?nsted acid catalysis. In this article, we present a comprehensive mechanistic investigation on this activation principle, which eventually led to its elucidation. Detailed studies are reported, including computational investigations on the supramolecular heterodimer, kinetic studies on the catalytic cycle, and a thorough analysis of transition states by DFT calculations for the rationalization of the catalyst structure-selectivity relationship. On the basis of these investigations, we developed a kinetic resolution of racemic epoxides, which proceeds with high selectivity (up to s = 93), giving the unreacted epoxides and the corresponding protected 1,2-diols in high enantiopurity. Moreover, this approach could be advanced to an unprecedented stereodivergent resolution of racemic α-chiral carboxylic acids, thus providing access to a variety of enantiopure nonsteroidal anti-inflammatory drugs and to α-amino acid derivatives.
- Monaco, Mattia Riccardo,Fazzi, Daniele,Tsuji, Nobuya,Leutzsch, Markus,Liao, Saihu,Thiel, Walter,List, Benjamin
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supporting information
p. 14740 - 14749
(2016/11/18)
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- Ti-salalen mediated asymmetric epoxidation of olefins with H2O2: Effect of ligand on the catalytic performance, and insight into the oxidation mechanism
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The highly enantioselective epoxidation of several conjugated olefins with H2O2 in the presence of five chiral titanium(IV) salalen (dihydrosalen) complexes has been studied, with focus on the effects of substituents (electronic and
- Talsi, Evgenii P.,Rybalova, Tatyana V.,Bryliakov, Konstantin P.
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p. 131 - 137
(2016/06/09)
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- Asymmetric epoxidation of unfunctionalized olefins accelerated by thermoresponsive self-assemblies in aqueous systems
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A novel thermoresponsive surfactant-type chiral salen MnIII catalyst was developed by axially grafting "smart" poly(N-isopropylacrylamide) (PNIPAAm) onto the metal center of a neat chiral salen MnIII complex. Characterization data su
- Zhang, Yaoyao,Tan, Rong,Zhao, Guangwu,Luo, Xuanfeng,Yin, Donghong
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p. 488 - 496
(2016/02/03)
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- Layered crystalline chiral salen Mn(III) complexes immobilized on organic polymer-inorganic hybrid zinc phosphonate-phosphate as efficient and reusable catalysts for the unfunctionalized olefin epoxidation
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Chiral Mn(III) salen complexes grafted on ZnPS-PVPA (zinc poly(styrene-phenylvinyl-phosphonate)-phosphate) upon alkyldiamines through a facile method are evaluated by the asymmetric epoxidation of unfunctionalized olefins. Superior catalytic performances
- Huang, Jing,Yuan, Li,Cai, Jiali,Chen, Xiaohong,Qi, Dengwei
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- Olefin epoxidation with chiral salen Mn(iii) immobilized on ZnPS-PVPA upon alkyldiamine
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The asymmetric epoxidation of unfunctionalized olefins using Jacobsen's catalyst is an effective strategy to achieve chiral epoxides. We report Jacobsen's catalysts anchored onto ZnPS-PVPA upon alkyldiamines as active heterogeneous catalysts for the epoxi
- Huang,Qi,Cai,Chen
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p. 19507 - 19514
(2016/03/01)
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- Constraining asymmetric organometallic catalysts within mesoporous supports ZnPS-BrPPAS boosts their enantioselectivity
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Novel layered heterogeneous chiral salen Mn(III) catalysts are synthesized with organic-inorganic hybrid material ZnPS-BrPPAS as the support and employed in the asymmetric epoxidations of unfunctionalized olefins. Characterizations indicate that the diffe
- Huang, Jing,Yuan, Li,Cai, Jiali
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p. 147 - 153
(2016/04/01)
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- Asymmetric epoxidation of unfunctionalized olefins catalyzed by Jacobsen's catalyst on alkoxyl-modified zirconium poly (styrene-phenylvinylphosphonate)-phosphate (ZPS-PVPA)
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New chiral Jacobsen's catalysts grafted onto alkoxyl-modified ZPS-PVPA are synthesized and applied in asymmetric epoxidations of unfunctionalized olefins. Specially, the supported catalysts indicate excellent catalytic activities (conv%, up to 96; sele%, up to 96; ee%, up to >99) in the absence of N-methylmorpholine N-oxide (NMO) by virtue of the special configurations of the catalysts. The superior stability (recycling for ten times) and the comfortable dispositions in large-scale reactions (such as 200 times) grant the potential application in industry to the heterogeneous catalysts.
- Huang, Jing,Luo, Yan,Cai, Jiali,Chen, Xiaohong
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- Discovery and Optimization of 1-Phenoxy-2-aminoindanes as Potent, Selective, and Orally Bioavailable Inhibitors of the Na+/H+ Exchanger Type 3 (NHE3)
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The design, synthesis, and structure-activity relationship of 1-phenoxy-2-aminoindanes as inhibitors of the Na+/H+ exchanger type 3 (NHE3) are described based on a hit from high-throughput screening (HTS). The chemical optimization resulted in the discovery of potent, selective, and orally bioavailable NHE3 inhibitors with 13d as best compound, showing high in vitro permeability and lacking CYP2D6 inhibition as main optimization parameters. Aligning 1-phenoxy-2-aminoindanes onto the X-ray structure of 13d then provided 3D-QSAR models for NHE3 inhibition capturing guidelines for optimization. These models showed good correlation coefficients and allowed for activity estimation. In silico ADMET models for Caco-2 permeability and CYP2D6 inhibition were also successfully applied for this series. Moreover, docking into the CYP2D6 X-ray structure provided a reliable alignment for 3D-QSAR models. Finally 13d, renamed as SAR197, was characterized in vitro and by in vivo pharmacokinetic (PK) and pharmacological studies to unveil its potential for reduction of obstructive sleep apneas.
- Rackelmann, Nils,Matter, Hans,Englert, Heinrich,Follmann, Markus,Maier, Thomas,Weston, John,Arndt, Petra,Heyse, Winfried,Mertsch, Katharina,Wirth, Klaus,Bialy, Laurent
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supporting information
p. 8812 - 8829
(2016/10/22)
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- A synergistic effect of a cobalt Schiff base complex and TiO2 nanoparticles on aerobic olefin epoxidation
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In this study, a cobalt Schiff base complex and TiO2 nanoparticles exhibited a synergistic effect on the visible-light photocatalytic activity in the aerobic oxidation of various olefins in the absence of a reducing agent. The catalyst structure was found to be well preserved after the oxidation reaction and the catalyst could be reused at least five times.
- Jafarpour, Maasoumeh,Kargar, Hossein,Rezaeifard, Abdolreza
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p. 79085 - 79089
(2016/09/09)
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- A process for the asymmetric epoxidation of olefins
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The invention provides an method for asymmetrically catalytically epoxidizing non-functionalized alkenes. A chiral complex formed by a tetra-dentate nitrogen organic ligand and a metal manganese manganese compound formation is employed as a catalyst, and
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Paragraph 0026-0029; 0034-0036
(2017/02/09)
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- Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes
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Enantiopure β-hydroxy sulfoxides and catechol sulfoxides were obtained, by chemoenzymatic synthesis, involving dioxygenase-catalysed benzylic hydroxylation or arene cis-dihydroxylation and cis-diol dehydrogenase-catalysed dehydrogenation. Absolute configurations of chiral hydroxy sulfoxides were determined by X-ray crystallography, ECD spectroscopy and stereochemical correlation. The application of a new range of β-hydroxy sulfoxides as chiral ligands was examined.
- Boyd, Derek R.,Sharma, Narain D.,Malone, John F.,Ljubez, Vera,Murphy, Deirdre,Shepherd, Steven D.,Allen, Christopher C. R.
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p. 2651 - 2664
(2016/03/05)
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- Self-supported chiral polymeric MnIII salen complexes as highly active and recyclable catalysts for epoxidation of nonfunctionalized olefins
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Abstract A series of self-supported chiral polymeric MnIII N,N′-ethylenebis(salicylimine) (salen) complexes were synthesized through metalation of the corresponding salen ligands obtained by condensation of several bis/tris-aldehydes with (1R,2
- Roy, Tamal,Kureshy, Rukhsana I.,Khan, Noor-Ul H.,Abdi, Sayed H. R.,Bajaj, Hari C.
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p. 1038 - 1044
(2015/06/08)
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- Discovery and pharmacological characterization of a novel potent inhibitor of diacylglycerol-sensitive TRPC cation channels
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Background and Purpose The cation channel transient receptor potential canonical (TRPC) 6 has been associated with several pathologies including focal segmental glomerulosclerosis, pulmonary hypertension and ischaemia reperfusion-induced lung oedema. We set out to discover novel inhibitors of TRPC6 channels and investigate the therapeutic potential of these agents. Experimental Approach A library of potential TRPC channel inhibitors was designed and synthesized. Activity of the compounds was assessed by measuring intracellular Ca2+ levels. The lead compound SAR7334 was further characterized by whole-cell patch-clamp techniques. The effects of SAR7334 on acute hypoxic pulmonary vasoconstriction (HPV) and systemic BP were investigated. Key Results SAR7334 inhibited TRPC6, TRPC3 and TRPC7-mediated Ca2+ influx into cells with IC50s of 9.5, 282 and 226 nM, whereas TRPC4 and TRPC5-mediated Ca2+ entry was not affected. Patch-clamp experiments confirmed that the compound blocked TRPC6 currents with an IC50 of 7.9 nM. Furthermore, SAR7334 suppressed TRPC6-dependent acute HPV in isolated perfused lungs from mice. Pharmacokinetic studies of SAR7334 demonstrated that the compound was suitable for chronic oral administration. In an initial short-term study, SAR7334 did not change mean arterial pressure in spontaneously hypertensive rats (SHR). Conclusions and Implications Our results confirm the role of TRPC6 channels in hypoxic pulmonary vasoregulation and indicate that these channels are unlikely to play a major role in BP regulation in SHR. SAR7334 is a novel, highly potent and bioavailable inhibitor of TRPC6 channels that opens new opportunities for the investigation of TRPC channel function in vivo.
- Maier,Follmann,Hessler,Kleemann,Hachtel,Fuchs,Weissmann,Linz,Schmidt,L?hn,Schroeter,Wang,Rütten,Strübing
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p. 3650 - 3660
(2015/07/02)
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- Reusable chiral salen Mn(III) complexes with phase transfer capability efficiently catalyze the asymmetric epoxidation of unfunctionalized olefins with NaClO
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A series of chiral salen Mn(III) polymers with build-in phase transfer capability was prepared by bridging the chiral salen Mn(III) units with polyethylene glycol (PEG)-based di-imidazolium ionic liquid (IL) side by side. Technologies of characterization
- Chen, Yaju,Tan, Rong,Zhang, Yaoyao,Zhao, Guangwu,Zheng, Weiguo,Luo, Rongchang,Yin, Donghong
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p. 106 - 115
(2015/05/05)
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- Reusable chiral salen Mn(III) complexes with phase transfer capability efficiently catalyze the asymmetric epoxidation of unfunctionalized olefins with NaClO
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A series of chiral salen Mn(III) polymers with build-in phase transfer capability was prepared by bridging the chiral salen Mn(III) units with polyethylene glycol (PEG)-based di-imidazolium ionic liquid (IL) side by side. Technologies of characterization
- Chen, Yaju,Tan, Rong,Zhang, Yaoyao,Zhao, Guangwu,Zheng, Weiguo,Luo, Rongchang,Yin, Donghong
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p. 106 - 115
(2015/05/04)
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- Catalytic epoxidation of cyclic alkenes with air over CoOx/zeolite heterogeneous catalysts
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The supported CoOx/zeolites have been prepared and applied for the epoxidation of cyclic alkenes with air. The catalysts are characterized by powder X-ray diffraction (XRD), ultraviolet-visible spectroscopy (UV-vis) and scanning electron microscope (SEM). Among these CoOx/zeolite catalysts, 2.4% CoOx/Y exhibits the best catalytic activity for the epoxidation of cis-cyclooctene with 61.2 mol% conversion and 98.8 mol% selectivity of epoxide. Some factors such as the kind of zeolites, the oxidants, the solvents, the Co contents, the reaction temperature and time play important roles in controlling the epoxidation. The recyclable stability of the 2.4% CoOx/Y catalyst is confirmed.
- Ma,Lu,Wei,Zhao,Zhan,Zhou,Xia
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- Catalytic performance of Keplerate polyoxomolybdates in green epoxidation of alkenes with hydrogen peroxide
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In this work, the catalytic perspective of three Keplerate polyoxometalates, Mo72M30 (M = V, Cr, Fe) in the epoxidation of various alkenes is considered. The catalytic reactions were performed in water under mild conditions and high to excellent conversions and selectivities were obtained using H2O2 as oxidant and Mo72Cr30 as the best catalyst. Keplerate POM catalysts have shown a very good recyclability, up to five times, without any appreciable decreases in catalytic activity and selectivity.
- Jalilian, Fariba,Yadollahi, Bahram,Riahi Farsani, Mostafa,Tangestaninejad, Shahram,Amiri Rudbari, Hadi,Habibi, Rouhollah
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p. 70424 - 70428
(2015/09/07)
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- Chemo-, regio-, and stereo-selective perfluoroalkylations by a Grignard complex with zirconocene
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The synthesis of highly reactive perfluoroalkyl Grignard reagents with early transition metal zirconocene complexes and their new types of highly chemo-, regio-, and stereo-selective perfluoroalkylation reactions are reported with epoxides in particular. The zirconocene complex is advantageous in activating the perfluoroalkyl Grignard species. The zirconocene·Grignard complexes were clarified by DOSY. Both 1H and 19F DOSY analyses show that the addition of MAO and dioxane to the mixture of RFMgCl and Cp2ZrCl2 connects Cp2Zr and RFMg to generate the zirconocene/perfluoroalkyl-Grignard/dioxane complex.
- Fujiu, Motohiro,Negishi, Kazuyuki,Guang, Jie,Williard, Paul G.,Kuroki, Shigeki,Mikami, Koichi
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supporting information
p. 19464 - 19468
(2015/11/27)
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- Attempts to prepare an all-carbon indigoid system
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First attempts are described to prepare a precursor for an all-carbon analog of indigo, the tetracyclic triene 4. Starting from indan-2-one (9) the α-methylene ketone 13 was prepared. Upon subjecting this compound to a McMurry coupling reaction, it dimerized to the bis-indene derivative 17, rather than providing the tetramethyl derivative of 4, the hydrocarbon 14. In a second approach, indan-1-one (18) was dimerized to the conjugated enedione 21 through the bis-1-indene dimer 19. All attempts to methylenate 21 failed, however. When 19 was treated with the Tebbe reagent, the dimer 23 was produced, presumably through a Cope reaction of the intermediately generated isomer 22. The bis-indene derivative 23 can be alkylated with 1,2-dibromoethane to produce a 1:1 mixture of the spiro compounds 24 and 25. Although 9 could be reductively dimerized to 30, the conversion of this olefin to 14 failed.
- Yildizhan, ?eref,Hopf, Henning,Jones, Peter G.
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supporting information
p. 363 - 372
(2015/06/16)
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- Manganese complexes with non-porphyrin N4 ligands as recyclable catalyst for the asymmetric epoxidation of olefins
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New chiral manganese complexes of N4 ligands derived from 2-acetylpyridine were prepared and used as catalysts in the enantioselective epoxidation of olefins, using H2O2 as an oxidant to give epoxides, with excellent conversions (up to 99%) and enantiomeric excess (up to 88%) within 1 h at 0°C. A detailed mechanistic study was undertaken based on the information obtained by single crystal X-ray, optical rotation, UV-Vis, CD spectra and kinetic studies, and revealed that the reaction is first order with respect to the concentration of catalyst and oxidant and independent of substrate concentration. The complex (0.1 mol%) was successfully subjected to recyclability experiments over 3 cycles in the epoxidation of styrene with H2O2 as an oxidant and acetic acid as an additive at 0°C with retention of performance.
- Maity, Nabin Ch.,Kumar Bera, Prasanta,Ghosh, Debashis,Abdi, Sayed H. R.,Kureshy, Rukhsana I.,Khan, Noor-Ul H.,Bajaj, Hari C.,Suresh
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p. 208 - 217
(2014/01/06)
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- Asymmetric epoxidation of olefins with hydrogen peroxide by an in situ-formed manganese complex
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Asymmetric epoxidation of a variety of cis, trans, terminal, and trisubstituted olefins in excellent yields (up to 94%) and enantioselectivities (>99% ee) by an in situ-formed manganese complex using H2O 2 has been developed. A relationship between the hydrophobicity of the catalyst imposed by ligand and the catalytic activity has been observed. The influence of the amount and identity of the acid additive was examined, and improved enantioselectivities were achieved through the use of a catalytic amount of a carboxylic acid additive.
- Dai, Wen,Shang, Sensen,Chen, Bo,Li, Guosong,Wang, Lianyue,Ren, Lanhui,Gao, Shuang
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p. 6688 - 6694
(2014/08/05)
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- A series of crystalline organic polymer-inorganic hybrid material zinc-phosphonate-phosphates synthesized in the presence of templates for superior performance catalyst support
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New types of organic copolymer-inorganic hybrid material zinc-phosphonate-phosphates are prepared with amines as templates. Notably, crystalline samples are obtained not with traditional methods but with simple reactions. Moreover, the samples are provide
- Huang, Jing,Cai, Jiali,Li, Chang Ming,Fu, Xiang Kai
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- COMPOUNDS AND METHODS FOR INHIBITING NHE-MEDIATED ANTIPORT IN THE TREATMENT OF DISORDERS ASSOCIATED WITH FLUID RETENTION OR SALT OVERLOAD AND GASTROINTESTINAL TRACT DISORDERS
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The present disclosure is directed to compounds and methods for the treatment of disorders associated with fluid retention or salt overload, such as heart failure (in particular, congestive heart failure), chronic kidney disease, end-stage renal disease,
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Page/Page column 102; 103
(2014/03/25)
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- Titanium salan catalysts for the asymmetric epoxidation of alkenes: Steric and electronic factors governing the activity and enantioselectivity
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A new insight into the highly enantioselective (up to > 99.5% ee ) epoxidation of olefins in the presence of chiral titanium(IV) salan complexes is reported. A series of 14 chiral ligands with varying steric and electronic properties have been designed, a
- Talsi, Evgenii P.,Samsonenko, Denis G.,Bryliakov, Konstantin P.
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supporting information
p. 14329 - 14335
(2015/01/09)
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- OXONE-ACETONE MEDIATED METAL FREE PREPARATION OF SYN-DIOLS
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The present invention disclose a simple and high yielding process of Oxone-acetone mediated metal free syn-dihydroxylation of benzo fused olefins of formula (II) to obtain library of dioxolo compounds of formula (I). The invention further disclsoe a simple and high yielding process of Oxone-acetone mediated metal free syn-dihydroxylation of stilbene and its derivatives of formula (III) thereof. Also disclosed herein is Wacker-type oxidation of benzo-fused olefins of formula (X). The invention further disclose compounds of formula (I) which can be useful for the treatment of HIV, cancer or malaria.
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Page/Page column 19
(2015/01/16)
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- V-doped titanium mixed oxides as efficient catalysts for oxidation of alcohols and olefins
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V/TiO2 nanoparticles were synthesized by a one-pot solution combustion method using ammonium metavanadate and titanyl nitrate as a source of vanadium and titanium, respectively. Atomic absorption spectroscopy (AAS), FT-IR, X-ray diffraction (XRD), scanning electron microscopy (SEM) and transmission electron microscopy (TEM) were employed to characterize the physicochemical properties of this compound. This compound shows efficient catalytic reactivity for epoxidation of olefins and oxidation of alcohols in the presence of H2O2 as an oxidant.
- Amini, Mojtaba,Naslhajian, Hadi,Farnia, S. Morteza F.
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p. 1581 - 1586
(2014/05/06)
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- A new halide-free efficient reaction-controlled phase-transfer catalyst based on silicotungstate of [(C18H37)2(CH 3)2N]3[SiO4H(WO5) 3] for olefin epoxidation, oxidation of sulfides and alcohols with hydrogen peroxide
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A new reaction-controlled phase-transfer catalyst based on silicotungstate of [(C18H37)2(CH3) 2N]3[SiO4H(WO5)3] for oxidation of hydrocarbons is developed. The catalyst is a new heteropoly compound with silicon as heteroatom, which is different to the previously reported reaction-controlled phase transfer catalysts that were composed of quaternary ammonium heteropolyoxotungstates of [π-C5H 5N(CH2)15CH3]3[PW 4O16] and [π-C5H5N(CH 2)15CH3]3[PW4O 32] with phosphorus as heteroatom. The oxidation of various alkenes (such as linear terminal olefins, internal olefins, cyclic olefins and unactivated alkenes) to epoxides, sulfides to sulfoxides and sulfones, alcohols to carbonyl compounds, are successfully catalyzed by this recyclable and environmentally benign catalyst using H2O2 as oxidant and ethyl acetate as solvent. This catalyst is not only capable of catalyzing homogeneous oxidation of organic substrates with unique reaction-controlled phase-transfer character, but also avoids the use of toxic solvents. The catalyst could be easily recovered and reused after reaction, and the epoxidation of cyclohexene was performed twenty times without obvious loss in activity. The fresh catalyst and the used one were characterized by ICP, IR, UV-vis, 29Si MAS NMR and 183W NMR in detail. the Partner Organisations 2014.
- Ma, Baochun,Zhao, Wei,Zhang, Fuming,Zhang, Yingshuai,Wu, Songyun,Ding, Yong
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p. 32054 - 32062
(2014/08/18)
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- Silica-coated magnetite nanoparticles stabilized simple Mn-tetraphenylporphyrin for aqueous phase catalytic oxidations with tert-butyl hydroperoxide
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An economic and environmentally friendly system for efficient and selective oxidation of industrially and biologically important substrates in water using tert-butyl hydroperoxide catalyzed by a new magnetically recoverable Mn-porphyrin was developed. The easily prepared heterogeneous catalyst was characterized by powder X-ray diffraction, transmission electron microscopy, scanning electron microscopy, FT-IR and UV-vis spectroscopy. The size of the catalyst was estimated to be about 10 nm. The thermal gravimetric analysis demonstrated that the nanocatalyst was thermally stable up to almost 300 °C. The reactivity, selectivity and scope of the reaction were investigated with a variety of olefins, saturated hydrocarbons, alcohols and organosulfur compounds. The reactions proceeded smoothly in the absence of surfactants, organic co-solvents and thus take place "on water". The separation and recycling of nanocatalyst as well as isolation of water-insoluble products were simple, effective and economical in this clean oxidation method.
- Rezaeifard, Abdolreza,Farshid, Parisa,Jafarpour, Maasoumeh,Moghaddam, Gholamreza Kardan
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p. 9189 - 9196
(2014/03/21)
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- Carbon Dioxide as a Protecting Group: Highly Efficient and Selective Catalytic Access to Cyclic cis-Diol Scaffolds
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The efficient and highly selective formation of a wide range of (hetero)cyclic cis-diol scaffolds using aminotriphenolate-based metal catalysts is reported. The key intermediates are cyclic carbonates, which are obtained in high yield and with high levels of diastereo- and chemoselectivity from the parent oxirane precursors and carbon dioxide. Deprotection of the carbonate structures affords synthetically useful cis-diol scaffolds with different ring sizes that incorporate various functional groups. This atom-efficient method allows the simple construction of diol synthons using inexpensive and accessible precursors and green metal catalysts and showcases the use of CO2 as a temporary protecting group. Protective Carbon: Aminotriphenolate complexes of FeIII and AlIII are highly efficient and selective catalysts for the conversion of functional (multi)cyclic oxiranes into the corresponding cis carbonates. Basic hydrolysis of the latter provides a series of useful cyclic cis-diol scaffolds in high yield. In this process, CO2 acts as both a temporary protecting group and an oxygen donor.
- Laserna, Victor,Fiorani, Giulia,Whiteoak, Christopher J.,Martin, Eddy,Escudero-Adán, Eduardo,Kleij, Arjan W.
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supporting information
p. 10416 - 10419
(2016/02/18)
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