- Revisit to Henry reaction by non conventional heterogeneous and efficient catalyst for nitroalcohol synthesis
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A sustainable, green and efficient process for the synthesis of 2-nitro alcohol derivatives from different substituted aromatic aldehydes with nitroalkane by stirring at ambient temperature with high product yield is reported. Adoption of very mild reaction conditions, use of Calcined Eggshell (CES) as natural catalyst and simple workup are expected to contribute to the development of environmentally benign synthetic method for Henry (nitroaldol) reaction. CES is ecologically safe, inexpensive, and attractive heterogeneous base catalyst obtained from renewable resources, thus opening a new perspective for this process. Graphical abstract: [Figure not available: see fulltext.]
- Jadhav, Swati D.,Patil, Rupesh C.,Jagdale, Ashutosh A.,Patil, Suresh S.
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p. 593 - 606
(2021/11/03)
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- Polymeric nanoassembly of imine functionalized magnetite for loading copper salts to catalyze Henry and A3-coupling reactions
-
Poly(ethylenimine) was grafted on the magnetite (Fe3O4) nanoparticles, and subsequently reacted with different aldehydes to form the imine functionalities (Fe3O4-Imine NPs). Thus formed Fe3O4/su
- Rathod, Prakash B.,Kumar, K.S. Ajish,Athawale, Anjali A.,Pandey, Ashok K.
-
-
- Nitration of Alkenes and Oxiranes with Nitrogen(IV) Oxide in Liquid and Supercritical Carbon Dioxide Media
-
Abstract: For the first time the reactions of radical nitration of alkenes and oxiranes with nitrogen dioxide in the liquid and supercritical carbon dioxide (sc-CO2) media were carried out. Using octene-1, styrene, and their derivatives as exam
- Ivanov, R. E.,Zharkov, M. N.,Zlotin, S. G.
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p. 209 - 212
(2022/02/22)
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- Hypercoordinated diorganoantimony(III) compounds of types [2-(Me2NCH2)C6H4]2SbL and [PhCH2N(CH2C6H4)2]SbL (L = Cl, ONO2, OSO2CF3). Synthesis, structure and catalytic behaviour in the Henry reaction
-
The compounds [2-(Me2NCH2)C6H4]2SbL (L = ONO2 (2), OSO2CF3 (3)) and [PhCH2N(CH2C6H4)2]SbL (L = ONO2 (5), OSO2CF3 (6)) were prepared by reacting [2-(Me2NCH2)C6H4]2SbCl (1) and [PhCH2N(CH2C6H4)2]SbCl (4), respectively, with the appropriate silver(I) salt in a 1:1 molar ratio. The new species 2–6 were structurally characterized in solution using multinuclear NMR and in the solid state using infrared spectroscopy. The solid-state structures for compounds 2, 4 and 6, as well as for the hydrolysis ionic product [{2-(Me2N+HCH2)C6H4}{2-(Me2NCH2)C6H4}SbOH][CF3SO3]? (3h) were determined using single-crystal X-ray diffraction. Medium to strong intramolecular N→ Sb interactions were observed in all these four compounds, thus resulting in hypercoordinated organoantimony(III) species 14-Sb-6 in 2 and 10-Sb-4 in the cation of 3h and in 4 and 6. Compounds 1–6 and the starting amines PhCH2NMe2 and PhCH2N(CH2C6H4Br-2)2 were investigated as catalysts in the Henry (nitroaldol) addition of nitromethane to benzaldehyde. The activity of compounds 1–6 resulted as an effect of the cooperation of the positively charged antimony with the negatively charged nitrogen.
- ?uteu, R?zvan,Candu, Natalia,Parvulescu, Vasile I.,Ra?, Ciprian I.,Simion, Andrada,Sivestru, Anca,Sivestru, Cristian
-
-
- Waste-to-useful: A biowaste-derived heterogeneous catalyst for a green and sustainable Henry reaction
-
Owing to the depletion of resources coupled with increasing waste generation, the conversion of waste biomass to value-added materials has gained interest. Here, we report for the first time the application of Musa acuminata (banana) peel ash (MAPA) as a heterogeneous catalyst for C-C bond formation via a Henry reaction under solvent-free conditions at ambient temperature. The catalyst was well characterized using different analytical techniques like FT-IR, SEM, TEM-EDS, XRD, XRF, XPS, BET and TGA, along with basicity determination by a Hammett indicator test and titration method. An excellent yield of nitroalcohol was obtained within 15-30 minutes. No dehydrated product was observed. The catalyst used in these studies has the advantage of being a waste material and is hence low-cost, easily prepared, recyclable and environmentally friendly. In addition, the use of a biogenic renewable catalyst, its atom economy, and room temperature and solvent-free reaction conditions and the avoidance of column chromatography make the protocol highly significant from green and sustainable chemistry perspectives.
- Rajkumari, Kalyani,Das, Diparjun,Pathak, Gunindra,Rokhum, Lalthazuala
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p. 2134 - 2140
(2019/02/05)
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- Synthesis, Characterization and Catalytic Activity of Magnetic KI@Fe3O4 Nanoparticles for Henry Reaction Under Solvent Free Conditions
-
Abstract: In this paper, we, for the first time reported the synthesis of KI loaded Fe3O4 nanoparticles (KI@Fe3O4 NPs) and investigated its applications in the synthesis of β-nitroalcohol via Henry reaction at room temperature under solvent-free conditions. The synthesized KI@Fe3O4 nanoparticle was characterized by SEM, HRTEM, XRD, XPS, EDX, VSM and FT-IR spectroscopy techniques. The XRD peaks at 2θ = 21.9, 25.65, 33.54, 36.35, 40.97, 42.81, 44.79, 54.43, 57.37, 58.83 and 63.13° corresponds to the formation of crystalline KI@Fe3O4 NPs. The activity of the catalyst by varying the amount of KI loading on Fe3O4 NPs was also investigated. Mild reaction conditions, good yield, short reaction time, solvent-free conditions, easy recoverability and recyclability of the nanocatalysts are the major advantages of our method. Graphical Abstract: [Figure not available: see fulltext.].
- Rokhum, Lalthazuala,Pathak, Gunindra
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p. 2887 - 2898
(2019/05/28)
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- Designing of a magnetically separable Fe3O4@dopa@ML nano-catalyst for multiple organic transformations (epoxidation, reduction, and coupling) in aqueous medium
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A copper(II) macrocyclic Schiff base complex (ML) was synthesized by condensation between 2,2-dimethylpropane-1,3-diammine and 2,6-diformyl-4-butylphenol with the aim to modify the surface of widely used magnetically separable nanocatalyst Fe3O
- Dasgupta, Sanchari,Chatterjee, Sourav,Chattopadhyay, Tanmay
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p. 550 - 568
(2019/02/26)
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- Design and development of novel Co-MOF nanostructures as an excellent catalyst for alcohol oxidation and Henry reaction, with a potential antibacterial activity
-
The novel metal–organic framework Co2(bdda)1.5(OAc)1·5H2O (UoB-3) was synthesized via a simple method at room temperature. UoB-3 was characterized by the different methods, including X-ray diffraction (XRD), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FT-IR), N2-adsorption/desorption and elemental analysis. The catalytic ability of UoB-3 was detected to be excellent for primary and secondary alcohols oxidation reaction with high yields under solvent-free conditions. Moreover, UoB-3 was highly active for Henry reaction of different aldehydes with nitromethane in water as a green solvent. The nanocatalyst can be recycled for five consecutive cycles without losing its activity and structural rigidity. The antibacterial activity of UoB-3 nanostructures towards Gram-negative bacteria, Escherichia coli and Gram-positive bacteria, Bacillus cereus was also evaluated by using an inhibition zone test. These nanostructures exhibited strong antibacterial effect against both of them. The purpose of this study was the developing metal–organic framework materials with the enhanced activity in various fields.
- Aryanejad, Sima,Bagherzade, Ghodsieh,Moudi, Maryam
-
-
- Synthetic Diversity from a Versatile and Radical Nitrating Reagent
-
We leverage the slow liberation of nitrogen dioxide from a newly discovered, inexpensive succinimide-derived reagent to allow for the C?H diversification of alkenes and alkynes. Beyond furnishing a library of aryl β-nitroalkenes, this reagent provides unparalleled access to β-nitrohydrins and β-nitroethers. Detailed mechanistic studies strongly suggest that a mesolytic N?N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, electron paramagnetic resonance spectroscopy, we observed direct evidence of a nitryl radical in solution by nitrone spin-trapping. To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C?H partners to prepare isoxazolines and isoxazoles is presented. This approach allows for the formation of an in situ nitrile oxide from a ketone partner, the presence of which is detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeds in a single-operational step using a mild, regioselective, and general protocol with broad chemoselectivity.
- Zhang, Kun,Jelier, Benson,Passera, Alessandro,Jeschke, Gunnar,Katayev, Dmitry
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supporting information
p. 12929 - 12939
(2019/09/17)
-
- Synthesis of functionalized carbon microspheres and their catalyst activity in C—O and C—N bond formation reactions
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Disclosed herein is a simple process for functionalization/grafting of carbon microspheres obtained from bagasse with various active functional groups onto it and use of the same as catalyst for various organic reactions, having very high selectivity and conversion rate.
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Page/Page column 8-9
(2019/02/14)
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- Ultrasonic-Assisted Linker Exchange (USALE): A Novel Post-Synthesis Method for Controlling the Functionality, Porosity, and Morphology of MOFs
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The introduction of organic ligands into metal–organic frameworks (MOFs) with a specific topology and that cannot be attained by direct synthesis is a big challenge. To meet this challenge, different ligand exchange/incorporation methods have been employed. Here, a new method, called ultrasonic-assisted linker exchange (USALE), has been developed to overcome the above-mentioned problems. USALE is a novel method for ligand exchange based on the use of ultrasonic waves. The temperature and pressure caused by the USALE method in microscopic zones are so intense that the linker exchange process is much faster than with other methods. In addition to saving time during synthesis, the use of the USALE method leads to a higher surface area and pore volume compared with other methods such as solvent-assisted linker exchange (SALE). In this way, improved gas adsorption capacity has been achieved for daughter frameworks synthesized by the USALE method. By using the USALE method, we have transformed a nonporous and easy-to-synthesize TMU framework ([Zn(OBA)(BPDB)0.5]n?2DMF (TMU-4), in which H2OBA=4,4′-oxybis(benzoic acid) and BPDB=1,4-di(4-pyridyl)-2,3-diaza-1,3-butadiene) into another porous framework ([Zn(OBA)(H2DPT)0.5]n?DMF (TMU-34), in which H2DPT=3,6-di(4-pyridyl)-1,4-dihydro-1,2,4,5-tetrazine) that otherwise requires a relatively long time to synthesize. In addition to reducing the synthesis time for TMU-34 (in comparison with both direct sonochemical synthesis and the indirect SALE method), the data obtained revealed that the daughter TMU-34 framework synthesized by the USALE method has a higher surface area and accessible pore volume than TMU-34 frameworks synthesized by SALE and direct methods. The application of SALE-TMU-34 and USALE-TMU-34 in a catalytic Henry condensation reaction and Congo Red adsorption experiments showed that the higher porosity of USALE-TMU-34 leads to a higher turn-over frequency and saturation capacity compared with SALE-TMU-34.
- Razavi, Sayed Ali Akbar,Morsali, Ali
-
supporting information
p. 10876 - 10885
(2019/08/01)
-
- Enantiomeric Resolution of Asymmetric-Carbon-Free Binuclear Double-Stranded Cobalt(III) Helicates and Their Application as Catalysts in Asymmetric Reactions
-
A series of double-stranded binuclear helicates [Co2(H1)2]4+, [Co2(H2)2]4+, and [Co2(H3)2]4+, derived from monodeprotonated bis-pyridyl hydrazine-based liga
- Arunachalam, Rajendran,Chinnaraja, Eswaran,Valkonen, Arto,Rissanen, Kari,Sen, Shovan K.,Natarajan, Ramalingam,Subramanian, Palani S.
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supporting information
p. 11414 - 11421
(2018/09/12)
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- Base-catalyzed reactions enhanced by solid acids: Amine-catalyzed nitroaldol (Henry) reactions enhanced by silica gel or mesoporous silica SBA-15
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The reactions of various aldehydes with CH3NO2 catalyzed by Et3N, n-C6H13NH2, and Me2N(CH2)2NH2 were accelerated by the addition of silica gel to give aromatic (aliphatic) β-nitroalcohols, aromatic nitroalkenes, and aromatic 1,3-dinitroalkanes, respectively. Mesoporous silica SBA-15 showed higher activity than silica gel for the synthesis of aromatic nitroalkenes by the reactions of the corresponding aldehydes with CH3NO2 catalyzed by n-C6H13NH2.
- Tanemura, Kiyoshi,Suzuki, Tsuneo
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supporting information
p. 392 - 396
(2017/12/28)
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- A 2 - amino - 3 - hydroxy pyridine hydrochloride preparation and synthetic method
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A chemical formula of 2-amidogen-3-hydroxy pyridine hydrochloride is shown as the accompanying drawing. A synthesis method of the compound (I) is characterized in that 2.2051g (0.02mol) of 2-amidogen-3-hydroxy pyridine is weighed and put into a 100mL roun
- -
-
Paragraph 0098; 0099; 0100
(2018/04/03)
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- Chemical Fixation of CO2 and Other Heterogeneous Catalytic Studies by Employing a Layered Cu-Porphyrin Prepared Through Single-Crystal to Single-Crystal Exchange of a Zn Analogue
-
A solvothermal reaction of Zn(NO3)2?6 H2O, tetra-(4-pyridyl)porphyrin (H2TPyP), and 4,4′-oxybis(benzoic acid) (H2OBA) resulted in a new two-dimensional Zn- porphyrin metal–organic framework compound,
- Dutta, Gargi,Jana, Ajay Kumar,Natarajan, Srinivasan
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supporting information
p. 66 - 72
(2017/12/07)
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- An ionic liquid gel: A heterogeneous catalyst for Erlenmeyer-Plochl and Henry reactions
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An ionic liquid gel has been prepared by entrapping 1-butyl-3-methylimidazolium hydroxide ([Bmim]OH) in an aqueous agar gel. The ionic liquid gel has been characterized by Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) spectroscopy, scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). The ionic liquid gel has been successfully employed as a heterogeneous catalyst in the Erlenmeyer-Plochl reaction involving aldehydes, hippuric acid and acetic anhydride as well as in the Henry reaction between aldehydes and nitromethane in ethanol at room temperature. The heterogeneity of the ionic liquid gel has been confirmed by conducting hot filtration tests and leaching studies. Additionally, the ionic liquid gel could be easily recovered by simple filtration and reused five times without significant loss in catalytic activity.
- Jagadale, Megha,Naikwade, Altafhusen,Salunkhe, Rajashri,Rajmane, Mohan,Rashinkar, Gajanan
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p. 10993 - 11005
(2018/07/06)
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- Synthesis of Metallomacrocycle and Coordination Polymers with Pyridine-Based Amidocarboxylate Ligands and Their Catalytic Activities towards the Henry and Knoevenagel Reactions
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The reactions of 3,3′-{(pyridine-2,6-dicarbonyl)bis(azanediyl)}dibenzoic acid (H2L) with zinc(II), cadmium(II), and samarium(III) nitrates were studied, and the obtained compounds, [Zn(1κO:2κO′-L)(H2O)2]n (1), [
- Karmakar, Anirban,Rúbio, Guilherme M. D. M.,Guedes da Silva, M. Fátima C.,Pombeiro, Armando J. L.
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p. 865 - 877
(2018/12/10)
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- Cu6S6 Clusters as a Building Block for the Stabilization of Coordination Polymers with NiAs, NaCl, and Related Structures: Synthesis, Structure, and Catalytic Studies
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Four new three-dimensional heterometallic coordination polymers (CPs), [{Zn3(Hen)(OH)}{Cu6(6-mna)6}·(H2O)6] (I), [{Zn2(OH)(en)}{Cu6(6-mna)6}0.5·(H2/su
- Jana, Ajay Kumar,Natarajan, Srinivasan
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p. 739 - 750
(2018/02/09)
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- A Continuous-Flow, Two-Step, Metal-Free Process for the Synthesis of Differently Substituted Chiral 1,2-Diamino Derivatives
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The enantioselective organocatalytic reduction of aryl-substituted nitroenamines was successfully performed under continuous-flow conditions. After a preliminary screening with a 10-μL microreactor, to establish the best reaction conditions, the reduction was scaled up in a 0.5-mL mesoreactor, without appreciable loss of enantioselectivity, that remained constantly higher than 90%. The in-flow nitro reduction was also accomplished, either by Raney nickel catalyzed hydrogenation or by a metal-free methodology based on the use of the very inexpensive and readily available reducing agent trichlorosilane. The final aim is to develop a two-step, continuous-flow process for the stereoselective, metal-free, catalytic synthesis of differently functionalized chiral 1,2-diamines.
- Pirola, Margherita,Compostella, Maria Elena,Raimondi, Laura,Puglisi, Alessandra,Benaglia, Maurizio
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supporting information
p. 1430 - 1438
(2018/02/09)
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- Chiral oxazoline palladium complex and application thereof
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The invention discloses a chiral oxazoline palladium complex. The chemical formula of the complex is as shown in the specification. A synthetic method of the complex comprises the following steps: enabling 50.75mmol of o-dicyanobenzene and 21.4037g of D-p
- -
-
Sheet 0067-0069
(2018/11/22)
-
- Copper(II) and Sodium(I) Complexes based on 3,7-Diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-oxide: Synthesis, Characterization, and Catalytic Activity
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The reaction of 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA) with metal salts of CuII or NaI/NiII under mild conditions led to the oxidized phosphane derivative 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-oxide (DAPTA=O) and to the first examples of metal complexes based on the DAPTA=O ligand, that is, [CuII(μ-CH3COO)2(κO-DAPTA=O)]2 (1) and [Na(1κOO′;2κO-DAPTA=O)(MeOH)]2(BPh4)2 (2). The catalytic activity of 1 was tested in the Henry reaction and for the aerobic 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO)-mediated oxidation of benzyl alcohol. Compound 1 was also evaluated as a model system for the catechol oxidase enzyme by using 3,5-di-tert-butylcatechol as the substrate. The kinetic data fitted the Michaelis–Menten equation and enabled the obtainment of a rate constant for the catalytic reaction; this rate constant is among the highest obtained for this substrate with the use of dinuclear CuII complexes. DFT calculations discarded a bridging mode binding type of the substrate and suggested a mixed-valence CuII/CuI complex intermediate, in which the spin electron density is mostly concentrated at one of the Cu atoms and at the organic ligand.
- Mahmoud, Abdallah G.,Guedes da Silva, M. Fátima C.,?liwa, Ewelina I.,Smoleński, Piotr,Kuznetsov, Maxim L.,Pombeiro, Armando J. L.
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p. 2868 - 2880
(2018/09/20)
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- Preparation method of 1-phenyl-2-nitroethanol and derivate thereof
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The invention discloses a preparation method of 1-phenyl-2-nitroethanol and a derivate thereof. The preparation method is characterized in that benzaldehyde or a derivate thereof and nitromethane aretreated as raw materials; tertiary butanol is treated as
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-
Paragraph 0019-0023; 0025-0029
(2019/01/14)
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- A nitroaryloxy aromatic preparation method (by machine translation)
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The invention discloses a nitroaryloxy aromatic preparation method, comprises the following steps: a, will R1 CHO, R2 CH2 NO2 , Catalyst and a polar organic solvent evenly, 0 °C -40 °C stirring for 6 hours -48 h
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-
Paragraph 0170; 0171; 0172; 0173; 0174; 0175; 0176-0213
(2017/05/23)
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- Biphenyl-Based Bis(thiourea) Organocatalyst for Asymmetric and syn -Selective Henry Reaction
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A scalable, efficient and chromatography-free synthesis of a new enantiopure C 2-symmetric bis(thiourea) catalyst was accomplished from a readily available starting material. The developed strategy could be conducted on a multi-gram scale. Both the prepared enantiomers of the bis(thiourea) organocatalyst have been tested in the asymmetric Henry reaction under thoroughly optimized conditions during which an unusual solvent effect on enantioselectivity was found. The corresponding adducts were obtained in excellent yields with good to excellent enantioselectivities. The achieved high reactivity and enantioselectivity in the nitroaldol reaction of nitroalkanes with aromatic aldehydes suggests promising potential for this catalyst. Moreover, a significant syn-diastereoselectivity was observed.
- Otevrel, Jan,Bobal, Pavel
-
supporting information
p. 593 - 603
(2017/01/25)
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- Synthesis, crystal structure of copper(II) complexes comprising 2-(biphenylazo)phenol and 1-(biphenylazo)naphthol ligands and their catalytic activity in nitroaldol reaction
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New series of copper(II) complexes of the type [Cu(L)2] (L = L1–L5) comprising bidentate 2-(biphenylazo)phenol (HL1–HL4) and 1-(biphenylazo)naphthol (HL5) ligands have been synthesized. The composition of complexes and ligands (HL1–HL4) has been established by elemental analysis and spectral (FT–IR, UV–Vis, 1H NMR and EPR) methods. Molecular structures of copper complexes [Cu(L3)2] (3) and [Cu(L5)2] (5) were established by X-ray crystallography. These Copper(II) biphenylazo complexes exhibit a very good catalytic activity towards nitroaldol reaction of various aldehydes with nitromethane.
- Nandhini, Raja,Ramesh, Madhan,Prabusankar, Ganesan,Venkatachalam, Galmari
-
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- A double-chiral amino alcohol compound and its preparation method and application
-
The invention discloses a bis-chiral alkamine compound and a preparation method therefor and application thereof. A chiral ligand is selected and synthesized to prepare a chiral catalyst. The chemical name of the compound is N,N'-bis[(1S)-2-hydroxyl-1-ary
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Page/Page column 0042; 0043; 0044; 0045; 0046
(2017/08/25)
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- A NbO type Cu(II) metal-organic framework showing efficient catalytic activity in the Friedl?nder and Henry reactions
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A three-dimensional NbO type porous metal-organic framework 1 containing both tertiary amine groups and paddle wheel dinuclear Cu2(COO)4 secondary building units as the active centre was synthesized at room temperature. The activated
- Gupta, Anoop K.,De, Dinesh,Bharadwaj, Parimal K.
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p. 7782 - 7790
(2017/07/11)
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- Solvent-Free Henry and Michael Reactions with Nitroalkanes Promoted by Potassium Carbonate as a Versatile Heterogeneous Catalyst
-
The use of a simple weak inorganic base such as potassium carbonate facilitated the formation of carbon-carbon bonds through both the Henry and the Michael reactions with nitrocompounds. The application of this catalyst under environmentally friendly solventless heterogeneous conditions gave satisfactory to good yields of β-nitroalcohols, involving aliphatic and aromatic starting materials, as well as high to excellent yields in the formation of Michael adducts using several different Michael acceptors and nitroalkanes.
- Bosica, Giovanna,Polidano, Kurt
-
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- A porous two-dimensional Zn(II)-coordination polymer exhibiting SC-SC transmetalation with Cu(II): Efficient heterogeneous catalysis for the Henry reaction and detection of nitro explosives
-
The linker 5-(benzylamino)isophthalic acid (H2L) forms a robust 2D Zn(ii)-coordination polymer, {[Zn8(L)6(μ3-OH)4(H2O)6]·(DMF)·(H2O)2.5}n(1Z
- Gupta, Mayank,De, Dinesh,Pal, Sanchari,Pal, Tapan K.,Tomar, Kapil
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supporting information
p. 7619 - 7627
(2017/07/10)
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- A amide preparation method of the compound
-
The invention discloses a preparation method for an amide compound. The method comprises the steps of: a. taking R1CHO and R2CH2NO2, adding a catalyst and R3CN, carrying out stirring reaction for 24h-48h at 0DEG C-40DEG C to obtain a reaction liquid; and
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-
Paragraph 0176; 0177; 0178; 0179; 0180; 0181; 0182-0218
(2017/06/02)
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- Henry reaction catalyzed by recyclable [C4dabco]OH ionic liquid
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DABCO-based ionic liquid, 1-butyl-4-aza-1-azaniabicyclo[2.2.2]octane hydroxide, has been used as an efficient catalyst for Henry reaction of various carbonyl compounds with nitroalkanes affording very high yields within a short duration. This method is very simple, clean and avoids hazardous organic solvents. The catalyst can be easily recovered and recycled several times.
- Keithellakpam, Sanjoy,Laitonjam, Warjeet S.
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p. 110 - 113
(2016/02/26)
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- Henry reaction catalyzed by recyclable [C4dabco]OH ionic liquid
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DABCO-based ionic liquid, 1-butyl-4-aza-1-azaniabicyclo[2.2.2]octane hydroxide, has been used as an efficient catalyst for Henry reaction of various carbonyl compounds with nitroalkanes affording very high yields within a short duration. This method is very simple, clean and avoids hazardous organic solvents. The catalyst can be easily recovered and recycled several times.
- Keithellakpam, Sanjoy,Laitonjam, Warjeet S.
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p. 110 - 113
(2017/01/18)
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- Polymer supported DMAP: An easily recyclable organocatalyst for highly atom-economical Henry reaction under solvent-free conditions
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Polymer supported catalysts are regarded as a borderline class of catalysts, which retains the advantages of homogeneous catalysts while securing the ease of recovery by simple filtration and workup of heterogeneous systems. Additionally, such catalysts are less hygroscopic due to the long polymer backbone. Here we have demonstrated that a catalytic amount of polymer supported DMAP (10 mol%) can lead to excellent conversion of an equimolar mixture of aldehyde and nitroalkane exclusively into β-nitroalcohols via the Henry reaction. Unlike most of the commonly used catalysts, polymer supported DMAP can be recovered by simple filtration and reused several times, thereby reducing the operational cost. High synthetic efficiency, total atom economy, near quantitative yields, mild reaction conditions, operational simplicity, easy recovery and reusability of the catalyst, solvent-free reaction conditions and avoidance of traditional reaction workup make the protocol highly significant from Green and Sustainable Chemistry perspectives.
- Das, Diparjun,Pathak, Gunindra,Rokhum, Lalthazuala
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p. 104154 - 104163
(2016/11/17)
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- Application of natural feedstock extract: The Henry reaction
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For the first time, we have successfully performed the Henry reaction in neat 'Natural Feedstock Extract' at room temperature. Herein, we used two most abundant natural feedstock extracts such as 'Water Extract of Banana' (WEB) and 'Water Extract of Rice Straw Ash' (WERSA). This protocol is highly advantageous owing to the employment of natural feedstock as green reaction media resulting in significant novelty and advancement with respect to green and sustainable chemistry.
- Surneni, Naresh,Barua, Nabin C.,Saikia, Bishwajit
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supporting information
p. 2814 - 2817
(2016/06/09)
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- Ba/ZrO2 nanoparticles as efficient heterogeneous base catalyst for the synthesis of β-nitro alcohols and 2-amino 2-chromenes
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Zirconia nanoparticles were synthesized by precipitation, urea hydrolysis, amorphous citrate and combustion synthesis methods. The zirconia surface was subsequently modified by grafting Ba 2+ species. The Ba 2+ modified zirconia (Ba/ZrO 2) materials were characterized using XRD, Fourier analysis, UV-vis-DRS, FESEM and HRTEM techniques. XRD study indicated selective stabilization of the tetragonal phase of zirconia in the presence of Ba 2+ species. Fourier line profile analysis of the XRD peaks revealed that the average crystallite size of the zirconia nanoparticles is in the range of 5-15 nm. The surface area, basicity and barium content of the material depend strongly on the method of synthesis. The Ba/ZrO 2 catalyst prepared by urea hydrolysis method exhibited higher surface area and barium content compared to other samples. The catalytic activity of the Ba/ZrO 2 catalyst was evaluated for synthesis of β-nitro alcohols and 2-amino 2-chromenes. The β-nitro alcohols were synthesized by condensation of aryl aldehydes and nitromethane. Similarly, the 2-amino 2-chromenes were synthesized by condensation of arylaldehydes, α-naphthol and malononitrile. The Ba/ZrO 2 catalyst was found to be highly efficient for synthesis of both classes of compounds providing excellent yield and purity of the products. [Figure not available: see fulltext.]
- Pradhan, Sagnika,Swarnima, Kumari,Mishra
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p. 1119 - 1130
(2016/07/15)
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- Mg-NHC complex on the surface of nanomagnesium oxide for catalytic application
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We have developed a simple and eco-friendly protocol for the synthesis of Mg-NHC complexes. The Mg-NHC complex is prepared by reacting nano-MgO with imidazolium salts. Thus prepared Mg-NHC complex has been realized in two divergent reactions one in C-C bond formation and other in dehydration reaction. Further, the Mg-NHC catalyst has been characterized by SEM, TEM, XPS, Raman Spectroscopy and XRD analysis.
- Shaikh, Melad,Sahu, Mahendra,Gavel, Pramod Kumar,Turpu, Goverdhan Reddy,Khilari, Santimoy,Pradhan, Debabrata,Ranganath, Kalluri V.S.
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- Cobalt complex preparation and synthesis method
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The invention discloses a cobalt complex and a synthesis method thereof. A chemical formula of a cobalt complex crystal is shown in the specification. The synthesis method of the cobalt complex (I) includes: weighing 0.5962g (0.005mol) of 2-cyano-5-aminop
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Paragraph 0033; 0034; 0035
(2016/10/10)
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- A chloroform-containing crystalline chiral zinc complex crystal and use
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The invention relates to a chiral zinc-nitrogen complex. The chemical formula of the chiral zinc-nitrogen complex is shown in the specification. A synthetic method of the chiral zinc-nitrogen complex (I) is characterized by comprising the following steps:
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Paragraph 0274; 0275; 0276
(2016/11/24)
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- Silver comes into play: Henry reaction and domino cycloisomerisation sequence catalysed by [Ag(i)(Pc-L)] complexes
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We report herein the synthesis of new pyridine-containing macrocyclic ligands (Pc-L) bearing a non-innocent pendant arm, by exploiting both chiral and functional properties of natural amino acids. The obtained macrocyclic ligands were employed to synthesize well-defined cationic silver(i) complexes that were shown to be competent catalysts for the Henry (nitroaldol) reaction. Good to excellent yields and full selectivity in the β-nitroalcohol product were obtained starting from electron-poor aromatic aldehydes or other activated aldehydes such as furfural under mild reaction conditions. The straightforward synthesis of the macrocyclic ligands starting from cheap commercially available starting materials allowed the introduction of a suitable basic functionality into the ligand pendant arm, thus providing a bifunctional catalyst. Based on our previous experience in the [Ag(i)(Pc-L)] catalysed domino addition/cycloisomerisation reaction of o-alkynylbenzaldehydes and nucleophiles, the synthesis of isochromenes coupling the Henry reaction and the cycloisomerisation in a single step was subsequently explored. Although with low selectivity, [Ag(i)(Pc-L)] cationic complexes were able to promote such a cascade reaction and a possible mechanism based on experimental evidence has been proposed.
- Tseberlidis, Giorgio,Dell'Acqua, Monica,Valcarenghi, Daniele,Gallo, Emma,Rossi, Elisabetta,Abbiati, Giorgio,Caselli, Alessandro
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p. 97404 - 97419
(2016/10/25)
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- Dendronized piperidine: Highly effective and recyclable catalysts for Henry reaction
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Two types of dendronized tertiary amines were synthesized by attaching piperidine to the core of a Fréchet-type dendrimer or to the end of an alkyl chain that is linked to the dendritic core. The relationship between structure and property of the catalysts in the Henry reaction of 2-nitrobenzaldehyde and nitromethane was established. It was observed that the attachment of piperidine to the dendritic sector by using a hexamethylene chain effectively avoids the scenario of dendritic shell encapsulation. And the 4-G3′ catalyst of third-generation with dendritic link exhibits excellent catalytic performance, and can be recycled ten times without a significant loss of activity.
- Yi, Bing,Yin, Yanyan,Yi, Ziqi,Zhou, Wei,Liu, Haitao,Tan, Nianyuan,Yang, Hai
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supporting information
p. 2320 - 2323
(2016/05/10)
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- Metal-Organic Frameworks with Pyridyl-Based Isophthalic Acid and Their Catalytic Applications in Microwave Assisted Peroxidative Oxidation of Alcohols and Henry Reaction
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Reactions of 5-{(pyridin-4-ylmethyl)amino} isophthalic acid (H2L1) with copper(II), zinc(II), and cadmium(II) were studied, and the obtained metal-organic frameworks (MOFs) [{Cu(L1)(DMF)}·DMF·H2O]n (1), [Zn(L1)(H2/su
- Karmakar, Anirban,Martins, Luísa M. D. R. S.,Hazra, Susanta,Guedes Da Silva, M. Fátima C.,Pombeiro, Armando J. L.
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p. 1837 - 1849
(2016/05/09)
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- One-pot protocol to synthesize N-(β-nitro)amides by tandem Henry/Ritter reaction
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A novel, efficient and atom economical one pot protocol for the synthesis of N-(β-nitro)amides has been described by combining the Henry reaction with the Ritter reaction. The designed products could be obtained from easily available aldehydes, nitroalkan
- Ai, Wensi,Shi, Ronghua,Zhu, Liyan,Jiang, Dehong,Ma, Xiaobo,Yuan, Jilan,Wang, Zhouyu
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p. 24044 - 24048
(2015/03/30)
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- Selective synthesis of nitroalcohols in the presence of Ambersep 900 OH as heterogeneous catalyst
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Abstract A green protocol has been developed for the selective synthesis of β-nitroalcohols using commercially available Ambersep 900 OH as reusable heterogeneous catalyst. The reaction between aldehyde and nitromethane was performed under solvent-free condition at room temperature within a short time (70-150 min) in the presence of 10 wt % of Ambersep 900 OH to produce corresponding nitroalcohols in high yield (72-91 %). After the reaction is over, the catalyst can be separated and reused (3 cycles) without appreciable loss in its activity.
- Lodh, Rajsekhar,Sarma, Manas Jyoti,Borah, Arun Jyoti,Phukan, Prodeep
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p. 969 - 972
(2015/02/19)
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- Diastereoselective nitroaldol reaction catalyzed by binuclear copper(II) complexes in aqueous medium
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Polydentate ligands 1 and 2, which incorporate a terminal pyridyl moiety and an oxygen-rich oxalate dihydrizide/malonic dihydrizide spacer moiety, as well as their binuclear metal complexes [Cu212] and [Cu222], which adopt a 1:1 metal/ligand ratio, were synthesized and characterized. Both complexes were screened for their catalytic activity in the nitroaldol reaction, in which [Cu212] worked efficiently as catalyst for both substituted benzaldehyde and pyridinecarboxaldehyde, whereas [Cu222] is highly substrate specific and showed activity towards nitro-substituted aldehydes and pyridinecarboxaldehyde. Furthermore, as helicates are intrinsically chiral, the stereochemical architecture in the binuclear double-stranded Cu2helicates as catalyst favored the diastereoselective syn product with nitroethane and nitropropane and their respective diastereoselectivities were determined by using 1H NMR spectroscopy.
- Arunachalam, Rajendran,Aswathi, Chirayil S.,Das, Anjan,Kureshy, Rukhsana I.,Subramanian, Palani S.
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p. 209 - 216
(2015/01/30)
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- Urea-pyridine bridged periodic mesoporous organosilica: An efficient hydrogen-bond donating heterogeneous organocatalyst for Henry reaction
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Hydrogen-bond donating (HBD) organocatalysts have been employed as an important class of catalysts for the activation of small molecules. However, the use of these catalysts was restricted on account of the self-aggregation of HBD-active species. In this work, a successful approach was developed to construct novel urea-pyridine bridged periodic mesoporous organosilica (PMO) to prevent the unwanted self-recognition and aggregation of urea-based catalytic center by spatial isolation, unleashing its HBD organocatalytic activity along with cooperative effect from the pyridine unit for efficient Henry reaction. The urea-pyridine bridged PMO catalyst presents high structural stability and high catalytic recyclability.
- Borah, Parijat,Mondal, John,Zhao, Yanli
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p. 129 - 134
(2015/08/06)
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- Diaminosilane-functionalized on silicate-stabilised hydrotalcite (MA-HTSi-DA): As potential catalyst for nitro-aldol condensation
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Diaminosilane was introduced into silicate-anion-intercalated hydrotalcite (HT-Si) using a post-synthesis method. The resulting functionalized materials possess surface basicity. The textural properties of the functionalized materials were systematically investigated through powder XRD, FTIR and MAS-NMR studies. The diamine-functionalized materials showed very good catalytic activity for the nitro-aldol condensation of benzaldehyde and nitromethane under solvent-free conditions. The materials showed comparable catalytic activity upon recycling.
- Thangaraj, Baskaran,Jayaraj, Christopher,Srinivasan, Radhakrishnan,Ayyamperumal, Sakthivel
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- Synthesis of supported Ru-nanoparticles for selective hydrogenation of carbonyl compounds
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Ru nanoparticles were successfully supported on molecular sieves and it was further characterized by sophisticated analytical methods such as transmission electron microscopy, energydispersive X-ray spectroscopy and nitrogen adsorption techniques. Transmission electron microscopy data confirmed, indicated the formation of metal oxide nanoparticles (4.5±2 nm) on the external surface of molecular sieves. Ru supported molecular sieves were applied as a catalyst for the hydrogenation of carbonyl compounds. Aldehydes as well as ketones were successfully hydrogenated in good yield and selectivity. Easy synthesis of air/moisture stable catalyst, hassle free reaction protocol (no requirement of aqueous work-up), 7 times catalyst recycling and additive free approach were the promising outcomes of the proposed work.
- Upadhyay, Praveenkumar,Srivastava, Vivek
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p. 528 - 533
(2015/10/05)
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- Indium-mediated debromination of gem -bromonitroalkanes under mild conditions in aqueous medium
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gem-Bromonitroalkanes are efficiently reduced into the corresponding dehalogenated products in excellent yields with indium metal in the presence of a palladium(0) catalyst and indium(III) chloride in aqueous medium. The addition of bromonitromethane to c
- Acúrcio, Rita C.,Soengas, Raquel G.,Silva, Artur M. S.
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p. 1561 - 1564
(2014/07/08)
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- Synthesis, spectral characterization and crystal structure of Ni(II) pyridoxal thiosemicarbazone complexes and their recyclable catalytic application in the nitroaldol (Henry) reaction in ionic liquid media
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The new square planar nickel(II) complexes 1, 2 and 3 have been synthesized from the reaction of [NiCl2(PPh3)2] with the tridentate Schiff base ligand, pyridoxal thiosemicarbazone (L1), pyridoxal N-methyl thiosemicarbazone (L2) and pyridoxal N-phenyl thiosemicarbazone (L3) respectively in ethanol. These complexes have been characterized by elemental analyses, IR, UV-Vis, 1H NMR, 31P NMR and ESI-MS spectroscopy. The molecular structure of the complex [Ni(L2)PPh3] (2) was determined by single-crystal X-ray diffraction, which reveals a distorted square planar geometry around the nickel(II) ion. The nitroaldol reaction was studied in detail using the nickel(II) complexes as catalysts in a homogeneous solution formed by an ionic liquid and methanol. The effect of solvent, ionic liquid, time, temperature, catalyst loading and substituent of the ligand moiety on the reaction was also studied. The β-nitroalcohol products were obtained in good yields of up to 97%. A two step substrate addition mechanism was tentatively proposed based on ESI-MS spectral monitoring of the reaction mass.
- Manikandan, Rajendran,Anitha, Panneerselvam,Prakash, Govindan,Vijayan, Paranthaman,Viswanathamurthi, Periasamy
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p. 619 - 627
(2014/11/07)
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