- Use of polyazaheterocycles in the assembly of new cadmium sulfate frameworks: Synthesis, structure, and properties
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The reaction of cadmium sulfate in the presence of polyazaheterocyclic organic molecules gave rise to a variety of new cadmium sulfate phases in water containing solvothermal reaction. The compounds have two- (I) and three-dimensionally (II-VI) extended s
- Paul, Avijit Kumar,Sanyal, Udishnu,Natarajan, Srinivasan
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Read Online
- High-throughput study of the Cu(CH3COO)2· H2O-5-nitroisophthalic acid-heterocyclic ligand system: Synthesis, structure, magnetic, and heterogeneous catalytic studies of three copper nitroisophthalates
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A high-throughput screening was employed to identify new compounds in Cu(CH3COO)2·H2O-NIPA-heterocyclic ligand systems. Of the compounds identified, three compounds, [Cu3{(NO 2)-C6H3/
- Sarma, Debajit,Ramanujachary,Stock, Norbert,Natarajan, Srinivasan
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- Aliphatic amine mediated assembly of [M6(mna)6] (M = Cu/Ag) into extended two-dimensional structures: synthesis, structure and Lewis acid catalytic studies
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Two new two-dimensional layered compounds, [{Ag6(2-mna)6Cd(Hen)2}{Cd(en)22H2O}(H2O)8],I, and [{M6(2-mna)6Cd(Hen)2}(H2en)(H2
- Sarkar, Anupam,Jana, Ajay Kumar,Natarajan, Srinivasan
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- PKU-3: An HCl-Inclusive Aluminoborate for Strecker Reaction Solved by Combining RED and PXRD
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A novel microporous aluminoborate, denoted as PKU-3, was prepared by the boric acid flux method. The structure of PKU-3 was determined by combining the rotation electron diffraction and synchrotron powder X-ray diffraction data with well resolved ordered
- Chen, Hong,Ju, Jing,Meng, Qingpeng,Su, Jie,Lin, Cong,Zhou, Zhengyang,Li, Guobao,Wang, Weilu,Gao, Wenliang,Zeng, Chunmei,Tang, Chiu,Lin, Jianhua,Yang, Tao,Sun, Junliang
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Read Online
- Synthesis and characterization of Pd supported on methane diamine (propyl silane) functionalized Fe3O4 nanoparticles as a magnetic catalyst for synthesis of α-aminonitriles and 2-methoxy-2-phenylacetonitrile derivative via Strecker-t
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Pd supported on methane diamine (propyl silane) functionalized Fe3O4 magnetic nanoparticles as an organic–inorganic hybrid heterogeneous catalyst was fabricated and characterized by FT-IR, XRD, SEM, TEM, TGA, VSM, EDX, and ICP-AES te
- Li, Qun,Liu, Wei,Mohammadnia, Majid,Song, Di,Sun, Mingzhe,Wu, Wei,Yan, Li
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- Catalytic Strecker reaction: g-C3N4-anchored sulfonic acid organocatalyst for the synthesis of α-aminonitriles
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Abstract: Efficient organocatalyst for enantioselective Strecker reaction was synthesized using g-C3N4 sheets (CN). CN-anchored sulfonic acid (CN-Bu-SO3H) was found to be a highly efficient and recoverable organocatalyst f
- Rahmati, Monavar,Ghafuri, Hossein
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p. 1489 - 1502
(2021/02/16)
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- Electrochemically promoted oxidative α-cyanation of tertiary and secondary amines using cheap AIBN
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The electrochemical α-cyanation of tertiary and secondary amines has been developed by using a cheap cyanide reagent, azobisisobutyronitrile (AIBN). The CN radical, generated throughn-Bu4NBr-meidated electrochemical oxidation, participates in a novel α-cyanation reaction under exogenous oxidant-free conditions.
- Cai, Tian-Cheng,Gui, Qing-Wen,Hu, Wenxia,Li, Qiang,Liu, Xiaoying,Teng, Fan,Wang, Xiaoli,Xiong, Zhi-Yuan,Yu, Jialing
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supporting information
p. 8254 - 8258
(2021/10/12)
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- Nitrile compound catalytic synthesis method and application thereof
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The invention relates to the technical field of chemical catalytic synthesis, and particularly discloses a nitrile compound catalytic synthesis method and application thereof. According to the nitrile compound catalytic synthesis method, an alpha-aminonitrile or alpha-imino nitrile compound can be synthesized through selective reaction. The nitrile compound catalytic synthesis method has the advantages of simple and easily available raw materials, wide substrate applicability, mild conditions, high yield and the like, the yield is superior to that of a traditional chemical synthesis method, and the nitrile compound catalytic synthesis method is suitable for industrial production. The problems that an existing synthesis method of alpha-aminonitrile and alpha-imino nitrile compounds is not high in yield and does not meet the requirement of green chemistry are solved. Moreover, compared with a traditional chemical synthesis method, a heme system is more efficient and green in use, a substrate is simple and easy to obtain, a tedious catalysis step is not needed, a low-toxicity cyano donor is used, the substrate is wide in applicability, the requirement of green chemistry is met, and the heme system has a wide market prospect.
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Paragraph 0109-0115
(2021/07/01)
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- Nano cobalt-copper ferrite catalyzed regioselective α-C(sp3)–H cyanation of amines: Secondary, tertiary, and drug molecules
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Oxidative cyanation of sp3C–H bonds at the α position of amines was achieved using CoCuFe2O4 as a catalyst and NaCN as an inexpensive cyanide source at room temperature. CoCuFe2O4 was found to be an active catalyst for Csp [3]-Csp coupling, efficiently delivering valuable α-aminonitriles from tertiary/secondary amines in good yields. The corresponding products were obtained with high selectivity toward α position. In addition, functional group tolerance offered the opportunity for application in late-stage functionalization of biologically active molecules. This transformation proceeds convenient on a gram-scale, and the catalyst can be reused for several runs with consistent catalytic activity.
- Heidarian, Mahdi,Moghaddam, Firouz Matloubi,Pourkaveh, Raheleh
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- A carbon dioxide-promoted three-component Strecker reaction
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A three-component Strecker reaction of aldehydes, amines and KCN has been performed for the first time in supercritical carbon dioxide. In the proposed procedure, non-toxic and non-flammable carbon dioxide acts not only as an environmentally benign reaction medium but also as a reaction promoter via in situ formation of carbonic acid which provides a gradual release of the true cyanating agent (HCN) from available KCN. The reaction conditions (pressure, temperature, and concentrations of reagents) were optimized, and various aromatic and aliphatic amines and aldehydes were transformed into valuable α-amino nitriles including prospective pharmacological substances. The equimolar amount of used cyanogen reagent, carrying out the process in a sealed autoclave in a 'green' solvent medium under mild conditions (90 bar, 35 °C) along with the high yields of products and the scalability of the developed procedure make it suitable for sustainable industrial applications. This journal is
- Fauziev, Ruslan V.,Ivanov, Roman E.,Kuchurov, Ilya V.,Zlotin, Sergei G.
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p. 10137 - 10144
(2021/12/24)
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- Cd-MOF@PVDF Mixed-Matrix Membrane with Good Catalytic Activity and Recyclability for the Production of Benzimidazole and Amino Acid Derivatives
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Mixed-matrix membranes (MMMs) incorporating metal-organic framework crystalline fillers as heterogeneous catalysts for organic transformation reactions have attracted more attention in catalysis science. Herein, a new 3D cadmium metal-organic framework (H3O)·[Cd(dppa)] (1) was first synthesized using the rigid 4-(3,5-dicarboxylphenyl)picolinic acid (H3dppa) as an organic ligand under solvothermal conditions, exhibiting a novel 6,6-connected network and good tolerance to various solvents. After activation, 1 showed good catalytic reactivity and selectivity for the synthesis of benzimidazole derivatives, affording solvent-dependent catalytic activity. Then, using the microcrystals of 1 and poly(vinylidene fluoride) (PVDF) as raw materials, 1@PVDF MMMs were successfully prepared by polymer solution casting. Notably, the integration of MOF and PVDF endows the mixed-matrix membrane 1@PVDF with great advantages in terms of more dispersive Lewis acid catalytic sites and recyclability. As expected, 1@PVDF not only displays good catalytic activity comparable to that of activated 1 but also exhibits remarkable recyclability and continuous usability for the production of benzimidazole and α-or β-amino acid derivatives. To the best of our knowledge, this is the first time that a Cd-based MOF and MMMs have been applied as a catalyst for the production of a β-amino acid. The combination of catalytic MOF and PVDF provides a way to simplify the design of a flow reactor and reduce the costs of manufacturing.
- Jiang, Yansong,Sun, Jing,Yang, Xiaona,Shen, Jieyu,Fu, Yu,Fan, Yong,Xu, Jianing,Wang, Li
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p. 2087 - 2096
(2021/02/06)
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- Cu/Ni-doped sulfated zirconium oxide immobilized on CdFe2O4 NPs: a cheap, sustainable and magnetically recyclable inorgano-catalyst for the efficient preparation of α-aminonitriles in aqueous media
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Abstract: A new multifunctional bimetallic nanocatalyst was prepared by immobilization of Cu/Ni-doped sulfated zirconium oxide on magnetic cadmium ferrite (CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni) and used as an efficient recyclable catalyst for one-pot as well as stepwise preparation of α-aminonitriles under mild conditions. The magnetic nanocatalyst was characterized by FTIR, TGA, VSM, XRD, EDX, FE-SEM, and TEM analyses. Also, the surface acidity of the catalyst was measured by pyridine adsorption assay. The catalyst possesses various active sites which could catalyst a variety of aromatic and aliphatic aldehydes to the corresponding α-amionitriles under moderate to high yields in the presence of aniline. Furthermore, transformation of ketones to the desired α-amionitriles and some bis-aminonitriles was also performed by this method. The catalyst could be readily recovered from the reaction mixture and reused for several times without significant loss of activity. Graphic abstract: A general and efficient method has been developed for transformation of a variety of aliphatic, aromatic aldehydes and ketones to the corresponding α-aminonitriles using a multifunctional recyclable CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni nanocatalyst.[Figure not available: see fulltext.]
- Nasseri, Mohammad Ali,Ramezani-Moghadam, Simin,Kazemnejadi, Milad,Allahresani, Ali
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p. 4233 - 4256
(2020/07/08)
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- Mandelic acid catalyzed one-pot three-component synthesis of α-aminonitriles and α-aminophosphonates under solvent-free conditions at room temperature
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A simple, mild, straightforward, efficient and eco-friendly protocol has been developed for the synthesis of a series of α-aminonitriles via the one-pot three-component Strecker reactions between various aldehydes, amines and trimethylsilyl cyanide using a catalytic amount of mandelic acid as a naturally occurring, low-cost, efficient organo-catalyst under solvent-free conditions at room temperature. Under the same optimized conditions synthesis of α-aminophosphonates were also achieved via the one-pot three-component Kabachnik-Fields reactions of aldehydes, amines and triethyl phosphate.
- Kaur, Gurpreet,Shamim, Mussarat,Bhardwaj, Vaishali,Gupta, Vivek Kumar,Banerjee, Bubun
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supporting information
p. 1545 - 1560
(2020/04/08)
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- KF/clinoptilolite nanoparticles as an efficient nanocatalyst for the Strecker synthesis of α-aminonitriles
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Abstract: Potassium fluoride impregnated on clinoptilolite nanoparticles (KF/CP NPs) have been explored to serve as an effective and inexpensive heterogeneous catalyst for the one-pot three-component Strecker synthesis of a variety of α-aminonitriles at room temperature in ethanol as a green solvent. KF/CP NPs have been synthesized using simple impregnation techniques in aqueous media from readily available inexpensive starting materials and displayed its initial catalytic activity even after five runs. The easy preparation and separation of catalyst, simple procedure, mild reaction conditions, and excellent yields of products render this method as an attractive sustainable option. Graphic abstract: [Figure not available: see fulltext.]
- Khalilzadeh, Mohammad A.,Oladee, Razieh,Zareyee, Daryoush
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- Targeted development of hydrophilic porous polysulfonamide gels with catalytic activity
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We report the use of a template and functional monomers in the synthesis of three novel polysulfonamide gels with new architectures and functional groups. These mesoporous polysulfonamide gels were prepared by the condensation polymerization of benzene-1,3-disulfonyl chloride (as the main precursor), linear monomers, and cross-linkers (as variable precursors) in the presence of a silica template by a combination of sol-gel chemistry and the nanocasting technique. In this synthesis pathway, in situ polymerization onto the template surface led to the construction of a silica/polymer nanocomposite. Next, after removal of the template, the nanocomposite gels were transformed into mesoporous polysulfonamide nanospheres. After the physicochemical identification of the synthesized materials, functionalized polysulfonamides were used as reusable novel catalysts with high efficiency for the Strecker reaction under mild conditions. These polymers have Br?nsted/Lewis acid active sites, a mesoporous structure, and hydrogen bonding. Moreover, since these polymers are hydrogels that can absorb water, they can promote the Strecker reaction through chemical absorption of the generated water as a driving force. Overall, this article describes a novel synthesis procedure and application of porous polysulfonamide gels.
- Alavinia, Sedigheh,Ghorbani-Vaghei, Ramin
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- Radical Rearrangement of Aryl/Alkylidene Malononitriles via Aza Michael Addition/Decynoformylation/Addition Sequence: An Access to α-Aminonitriles and α-Aminoamides
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An efficient, safe, and environmentally friendly tertiary butyl hydrogen peroxide (TBHP)-mediated rearrangement of aryl/alkylidene malononitrile with anilines has been developed with in situ generation of HCN as the cyanide source for the synthesis of sub
- Bhoite, Shubhangi P.,Bansode, Ajay H.,Suryavanshi, Gurunath
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p. 14858 - 14865
(2020/12/02)
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- Fe3O4?SiO2 nanoparticles–functionalized Cu(II) Schiff base complex with an imidazolium moiety as an efficient and eco-friendly bifunctional magnetically recoverable catalyst for the Strecker synthesis in aqueous media at room temperature
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Cu(II) Schiff base complex supported on Fe3O4?SiO2 nanoparticles was employed as a magnetic nanocatalyst (nanocomposite) with a phase transfer functionality for the one-pot preparation of α-aminonitriles (Strecker reaction). The desired α-aminonitriles were obtained from the reaction of aromatic or aliphatic aldehydes, aniline or benzyl amine, NaCN, and 1.6 mol% of the catalyst in water at room temperature and good to excellent yields were obtained for all substrates. The catalyst was characterized analytically and instrumentally including Fourier-transform infrared spectroscopy, X-ray diffraction, thermogravimetric, nuclear magnetic resonance, energy-dispersive X-ray spectroscopy, inductively coupled plasma spectroscopy, vibrating-sample magnetometry analysis, dynamic light scattering, Brunauer–Emmett–Teller surface area, field emission scanning electron microscopy, and transmission electron microscopy analyses. The reaction mechanism was investigated, in which the performance of the catalyst as a phase transition factor seems to be probable. The catalyst showed high activity, high turnover frequency (TOF)s, significant selectivity, and fast performance toward the Strecker synthesis. The nanocatalyst can be readily and quickly separated from the reaction mixture with an external magnet and can be reused for at least seven successive reaction cycles without significant reduction in efficiency.
- Kazemnejadi, Milad,Alavi G., Seyyedeh Ameneh,Rezazadeh, Zinat,Nasseri, Mohammad Ali,Allahresani, Ali,Esmaeilpour, Mohsen
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- Role of aromatic: Vs. aliphatic amine for the variation of structural, electrical and catalytic behaviors in a series of silver phosphonate extended hybrid solids
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Four inorganic-organic hybrid silver phosphonate compounds, [Ag(C10H8N2)(H4hedp)] (1), [Ag2(C10H8N2)(H3hedp)]·2H2O (2), [C4H12N2][Ag4(H2hedp)2] (3) and [C4H12N2][Ag10(H2hedp)4(H2O)2]·2H2O (4) (H5hedp = 1-hydroxyethane-1,1-diphosphonic acid), have been pre
- Rom, Tanmay,Paul, Avijit Kumar
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supporting information
p. 13618 - 13634
(2020/10/26)
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- Triggering Lewis Acidic Nature through the Variation of Coordination Environment of Cd-Centers in 2D-Coordination Polymers
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The rational design and successful synthesis of novel functional metal-organic frameworks relies on careful selection of metals and versatile organic ligands. A newly designed pyrazole-based dicarboxylate ligand, 5-(3,5-dimethyl-1H-pyrazol-1-yl) 1,3-benze
- Kumar, Nikhil,Paul, Avijit Kumar
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supporting information
p. 1284 - 1294
(2020/02/04)
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- Transition Metal Ions Regulated Structural and Catalytic Behaviors of Coordination Polymers
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Three new coordination polymers (CPs), I [Cu(L)(H2O)]·2H2O, II [Zn(L)], and III [Ag(HL)(CH3CN)], were synthesized by employing a novel pyrazole-based dicarboxylate ligand (H2L) through a solvothermal strategy. Single-crystal structural analysis established that compounds I and II exhibit two-dimensional (2D) sheet structures, while compound III possesses a one-dimensional (1D) ladder structure due to the connectivity of terminal solvent moiety. The geometries of metal ions vary from square planar (Cu2+ ion) to distorted tetrahedral (Zn2+ and Ag+ ion). Topological study showed that compound I has made a (4·62)2(42·62·82) net, while compounds II and III have exposed common (44·62) SQL net and (42·6) net, respectively. The Lewis acidic nature of compounds I, II, and III has been confirmed with various heterogeneous catalytic reactions. For the first time, one-pot multicomponent synthesis of α-amino amidine has been performed by the three CPs and the reaction kinetics has been altered by the variation of Lewis acidic metal centers. The roles of metal ions for structural variations and the catalytic performances are investigated in a series of CPs.
- Kumar, Nikhil,Rom, Tanmay,Singh, Virender,Paul, Avijit Kumar
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p. 5277 - 5288
(2020/09/09)
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- Cyano-borrowing: Titanium-catalyzed direct amination of cyanohydrins with amines and enantioselective examples
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The direct amination of cyanohydrins with amines via a catalytic cyano-borrowing reaction was developed. The transformation features broad substrate scope, excellent functional group compatibility, and very mild and simple operations. Moreover, a titanium
- Li, Qian,Li, Qing-Hua,Li, Wan-Fang,Li, Zhao-Feng,Liu, Tang-Lin,Peng, Yun-Gui,Ren, Li-Qing,Tao, Jing
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supporting information
p. 651 - 654
(2020/01/28)
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- A N - aryl methylaniline of α - carbonitriding method
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A N - aryl methylaniline of α - carbonitriding method. This law to various N - aryl aniline derivatives as raw materials, trimethylsilyl cyanide as the cyanide reagent, 2, 3 - dichloro - 5, 6 - dicyano - 1, 4 - benzoquinone as oxidizing agent in a solvent reaction after concentration, purification of a simple process to get the finished product. The purpose is for the existing N - aryl aniline oxidation carbonitriding method of deficiencies, provide a new synthesis method. The method adopts the low price, low toxicity, and easily obtained 2, 3 - dichloro - 5, 6 - dicyano - 1, 4 - benzoquinone as the oxidizing agent, the non-metal ion catalysis, high-efficiently the various N - aryl methylaniline with three oxidation of trimethylsilyl cyanide. The method of the invention the process is simple, preparing the reaction production safety, easy operation, reaction time is short, favorable to the industrialized.
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Paragraph 0022-0096
(2019/07/04)
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- Divergent Multistep Continuous Synthetic Transformations of Allylic Alcohol Enabled by Catalysts Immobilized in Ionic Liquid Phases.
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Two individual catalytic platforms (metal- and organo-catalyzed) based on the use of an ionic liquid phase were successfully integrated for the synthesis of α-cyano-amine and cyanohydrin trimethylsilyl ethers from allylic alcohol. The right combination of continuous flow processes enabled access to the divergent preparation of two alternative and interesting intermediate compounds from the same starting material.
- Peris, Edgar,Porcar, Raúl,García-álvarez, Joaquín,Burguete, María Isabel,García-Verdugo, Eduardo,Luis, Santiago V.
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p. 1684 - 1691
(2019/04/03)
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- Gallic acid grafted to amine-functionalized magnetic nanoparticles as a proficient catalyst for environmentally friendly synthesis of α-aminonitriles
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An effective approach of one-pot catalytic Strecker reaction between aromatic aldehydes, aniline or toluidine and trimethylsilyl cyanide in the presence of amine-functionalized Fe3O4@SiO2 nanoparticles grafted with gallic
- Maleki, Ali,Azadegan, Sepide,Rahimi, Jamal
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- Synthesis and characterization of an acidic nanostructure based on magnetic polyvinyl alcohol as an efficient heterogeneous nanocatalyst for the synthesis of α-aminonitriles
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The present study described design, preparation and characterization of a new magnetic nanocomposite based on polyvinyl alcohol (PVA) as a non-toxic, water-soluble, high mechanical stable and low-cost polymer. Fourier transform infrared (FT-IR) spectroscopy, field-emission scanning electron microscopy (FE-SEM) image, transmission electron microscope (TEM) image, X-ray diffraction (XRD) pattern, energy-dispersive X-ray (EDX) analysis and thermogravimetric (TG) analysis were used to describe the morphological, chemical and physical properties of the prepared nanocatalyst. All these results confirmed the successful synthesis of Fe3O4@PVA-SO3H. This heterogeneous nanocatalyst was then successfully used for the synthesis of α-aminonitrile derivatives by starting from an aldehyde, an aniline and trimethylsilyl cyanide (TMSCN). High efficiency, green chemistry properties, simple and easy separation are the specific properties of this nanocomposite. Fe3O4@PVA-SO3H can be derived out by an external magnet and reused ten times without any changes in its structure.
- Maleki, Ali,Rahimi, Jamal,Hajizadeh, Zoleikha,Niksefat, Maryam
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- Gallic acid-functionalized magnetic nanoparticles: a convenient and green approach for synthesis of α-aminonitriles under solvent-free conditions
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Abstract: Gallic acid-coated magnetic nanoparticles were efficiently prepared, characterized by Fourier transform infrared spectroscopy, X-ray diffraction, vibrating sample magnetometry, scanning electron microscopy, and transmission electron microscopy, and employed as an environmentally friendly and recyclable catalyst for one-pot synthesis of three-component reaction via Strecker reaction, incorporating aldehydes/ketones, amines, and trimethylsilyl cyanides under solvent-free conditions. Operational simplicity, product purity, natural resources and reusability of the catalyst are considered as evident features of this protocol which will hopefully develop into an inexpensive, efficient, and clean strategy for the synthesis of α-aminonitriles. Graphical abstract: [Figure not available: see fulltext.].
- Eidi, Esmaiel,Kassaee, Mohamad Z.,Nasresfahani, Zahra,Cummings, Peter T.
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p. 303 - 314
(2018/10/15)
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- Efficient synthesis of α-aminonitriles over homopiperazine sulfamic acid functionalized mesoporous silica nanoparticles (MSNs-HPZ-SO3H), as a reusable acid catalyst
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Abstract: Good to excellent yields of α-aminonitriles are achieved through three-component Strecker reaction of aldehydes or ketones with amines and trimethylsilyl cyanides over homopiperazine sulfamic acid functionalized mesoporous silica nanoparticles (MSNs-HPZ-SO3H). The advantages of this protocol include: simplicity, short reaction time, high yields, ease of product isolation and reusability of the catalyst. Graphical abstract: MSNs-HPZ-SO3H is prepared as an acid catalyst and successfully used for three-component Strecker reaction of aldehydes or ketones with amines and trimethylsilyl cyanides (TMSCN) under solvent-free conditions, a straightforward strategy for the synthesis of α-aminonitriles.[Figure not available: see fulltext.].
- Nasresfahani, Zahra,Kassaee, Mohamad Z.,Eidi, Esmaiel
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p. 1819 - 1825
(2019/04/17)
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- Design and Construction of a Chiral Cd(II)-MOF from Achiral Precursors: Synthesis, Crystal Structure and Catalytic Activity toward C-C and C-N Bond Forming Reactions
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Using achiral components, a V-shaped dicarboxylic acid (H2L) and a conformationally flexible bidentate linker (bpp), a thermally stable chiral metal organic framework {[Cd(bpp)(L)(H2O)]·DMF}n (1), where H2L = 4,
- Gupta, Vijay,Mandal, Sanjay K.
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p. 3219 - 3226
(2019/03/28)
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- Synthesis of 1-(α-aminoalkyl)-2-naphthol and α-aminonitrile derivatives with molybdenum Schiff base complex covalently bonded on silica-coated magnetic nanoparticles and DNA interaction study of one type of derivatives using computational and spectroscopi
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An air- and moisture-stable molybdenum Schiff base complexes immobilized on magnetic iron oxide nanoparticles with a core-shell structure was developed for utilization as a new heterogeneous catalyst. The surface, structural and magnetic characteristics o
- Rakhtshah, Jamshid,Shaabani, Behrouz,Salehzadeh, Sadegh,Hosseinpour Moghadam, Neda
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p. 420 - 430
(2019/01/23)
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- A Facile Approach to Catalyst-Free Cyanation and Azidation of a-Organic Compounds and a One-Pot Preparation of 5-Substituted 1 H-Tetrazoles by Using a Dimethyl Sulfoxide-Nitric Acid Combination
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In this study, cyanations or azidations of imines were performed by using hydroxy(dimethyl)-λ 4-sulfanecarbonitrile or azido(dimethyl)-λ 4-sulfanol, respectively, prepared in situ by treatment of potassium cyanide or sodium azide with a dimethyl sulfoxide-nitric acid combination. Furthermore, a one-pot preparation of 5-substituted 1 H-tetrazole derivatives was carried out by using this reagent combination in the presence of an aldehyde, hydroxylamine hydrochloride, and sodium azide under mild conditions.
- Alavi, Seyyedeh Ameneh,Kazemnejadi, Milad,Mahmoudi, Boshra,Nasseri, Mohammad Ali
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p. 2290 - 2294
(2019/12/11)
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- HCN on Tap: On-Demand Continuous Production of Anhydrous HCN for Organic Synthesis
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A continuous process for the on-demand generation, separation, and reaction of hydrogen cyanide (HCN) using membrane separation technology was developed. The inner tube of the reactor is manufactured from a gas-permeable, hydrophobic fluoropolymer (Teflon AF-2400) membrane. HCN is formed from aqueous reagents within the inner tube and then diffuses through the membrane into an outer tubing containing organic solvent. This technique enabled the safe handling of HCN for three different organic transformations without the need for distillation.
- K?ckinger, Manuel,Hone, Christopher A.,Kappe, C. Oliver
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supporting information
p. 5326 - 5330
(2019/09/06)
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- Synthesis of α-Aminonitriles and 5-Substituted 1H-Tetrazoles Using an Efficient Nanocatalyst of Fe3O4@SiO2–APTES-supported Trifluoroacetic Acid
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Fe3O4@SiO2–APTES-supported trifluoroacetic acid nanocatalyst was used for the one-pot synthesis of α-aminonitriles via a three-component reaction of aldehydes (or ketones), amines, and sodium cyanide. This method produced a high yield of 75–96% using only a small amount of the catalyst (0.05?g) in EtOH at room temperature. The catalyst was also employed for the synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide in EtOH at 80°C. The tetrazoles were produced with good-to-excellent yields in a short reaction time of 4?h. Both synthetic methods were carried out in the absence of an organic volatile solvent. Because the supported trifluoroacetic acid generated a solid acid on the surface, thus the acid corrosiveness was not a serious challenge. This heterogeneous nanocatalyst was magnetically recovered and reused several times without significant loss of catalytic activity.
- Fatahi, Hosna,Jafarzadeh, Mohammad,Pourmanouchehri, Zahra
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p. 2090 - 2098
(2019/07/05)
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- Strecker reactions with hexacyanoferrates as non-toxic cyanide sources
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The Strecker reaction is the most widely applied three-component reaction. Although highly useful for the preparation of α-amino nitriles, α-amino acids, hydantoins and numerous related compounds, the need for the application of toxic sources of HCN limits its application in both academic and industrial settings. Here, we present a facile protocol for Strecker reactions using a mixture of potassium ferri- and ferrocyanides as a non-toxic substitute.
- Grundke, Caroline,Opatz, Till
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supporting information
p. 2362 - 2366
(2019/05/17)
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- A unique combination of KI/ZnFe2O4 as a catalyst for oxidative Strecker reaction
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α-Aminonitriles as key intermediates for the preparation of α-amino acid derivatives, amides, diamines, peptides, proteins and heterocycles were synthesized through methylarene oxidation in the Strecker reaction using a unique combination of KI/ZnFe2O4 as the best catalyst and aqueous tert-butyl hydroperoxide as oxidant. A wide range of amines and methylarenes were converted to the corresponding products. Operational simplicity, short reaction time and recyclability of the catalyst are advantages of this protocol.
- Ghandi, Leila,Kazemi Miraki, Maryam,Karimi, Meghdad,Radfar, Iman,Heydari, Akbar
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- Enantioselective Strecker and Allylation Reactions with Aldimines Catalyzed by Chiral Oxazaborolidinium Ions
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Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various α-aminonitriles and homoallylic amines were synthesized in high yi
- Kang, Ki-Tae,Park, Sang Hyun,Ryu, Do Hyun
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supporting information
p. 6679 - 6683
(2019/09/12)
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- Three helical chain-based 3D coordination polymers: Solvent-induced syntheses, tunable structures and catalytic properties for the Strecker reaction
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Three three-dimensional (3D) helical chain-based coordination polymers [Sc(aip)(OH)·(H2O)]n (1), [Sc2(aip)3]n (2) and [Sc2(nip)3]n (3) (H2aip = 5-aminoisoph
- Chai, Juan,Zhang, Ping,Shi, Xiangxiang,Sun, Jing,Wang, Li,Fan, Yong
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p. 5440 - 5447
(2019/09/30)
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- Cross-dehydrogenative coupling strategy for phosphonation and cyanation of secondary N-alkyl anilines by employing 2,3-dichloro-5,6-dicyanobenzoquinone
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The cross-dehydrogenative coupling strategy for metal-free phosphonation and cyanation of secondary N-alkyl anilines has been developed firstly under mild reaction conditions. Based on detailed optimization of reaction conditions, the substrate generality of N-alkyl anilines and various hydrogen phosphonates has been investigated, and a series of versatile α-aminophosphonates and α-aminonitriles were therefore furnished in good to excellent yields. A plausible collective reaction mechanism through dehydrogenation to imine formation, then to respective α-aminophosphonates and α-aminonitriles was proposed.
- Liu, Qing,Yu, Shuchen,Hu, Liangzhen,Hussain, Muhamad Ijaz,Zhang, Xiaohui,Xiong, Yan
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supporting information
p. 7209 - 7217
(2018/11/10)
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- Fe3O4/MIL-101(Fe) nanocomposite as an efficient and recyclable catalyst for Strecker reaction
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A highly porous metal-organic framework, MIL-101(Fe), was prepared by a solvothermal method in the presence of amino-modified Fe3O4@SiO2 nanoparticles, in order to achieve Fe3O4/MIL-101(Fe) nanocomposite, which was characterized by XRD, FT-IR, SEM, TEM, BET, and VSM. This hybrid magnetic nanocomposite was employed as heterogeneous catalyst for α-amino nitriles synthesis through three-component condensation reaction of aldehydes (ketones), amines, and trimethylsilyl cyanide in EtOH, at room temperature. The recoverability and reusability was admitted for the heterogeneous magnetic catalyst; no significant reduction of catalytic activity was observed even after five consecutive reaction cycles.
- Mostafavi, Mohammad Mahdi,Movahedi, Farnaz
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- A Metal-Organic Framework to CuO Nanospheres of Uniform Morphology for the Synthesis of α-Aminonitriles under Solvent-Free Condition along with Crystal Structure of the Framework
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Herein, we have reported the synthesis, crystal structure, thermogravimetric property, and photoluminescence activity of a new Cu-based metal organic framework (MOF): {[Cu2(2,5-pdc)2(ald-4)(H2O)2]·3H2
- Singha, Soumen,Saha, Arijit,Goswami, Somen,Dey, Sanjoy Kumar,Payra, Soumen,Banerjee, Subhash,Kumar, Sanjay,Saha, Rajat
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p. 189 - 199
(2018/01/12)
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- Three-component solventless Strecker synthesis of α-aminonitriles catalysed by a renewable sulfonated nanoporous carbon catalyst (CMK-5-SO3H)
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The one-pot three-component synthesis of a variety of α-aminonitriles has been studied using a catalytic amount of a sulfonic acid-functionalized ordered nanoporous carbon catalyst, CMK-5-SO3H, at room temperature under solvent-free reaction co
- Zareyee, Daryoush,Rad, Ali Shokuhi,Ataei, Zahra,Javadi, Sayed Hossein,Khalilzadeh, Mohammad A.
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- Copper-vitamin B6 coated on maghemite nanoparticles: A new convenient dual catalysis system to synthesize α-aminonitriles from benzyl alcohols
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A novel and effective dual catalysis system, copper combined with pyridoxal phosphate, which is anchored in maghemite nanoparticles were designed and applied to synthesize α-aminonitriles from benzyl alcohols. This catalytic system has the potential ability to perform oxidation reactions and subsequently synthesize alpha-amino nitrile in a reaction environment. Thus, the purpose of this paper is introducing a heterogeneous, sustainable and recyclable catalytic system to perform reactions that require a transition metal catalyst and organocatalyst continuously to achieve a target molecule. The catalysis system is examined and investigated with seven useful analyses such as FT-IR, TGA, VSM, SEM, TEM, XRD, and ICP.
- Esfandiary, Naghmeh,Nakisa, Athar,Radfar, Iman,Azizi, Kobra,Mehraban, Jamshid Azarnia,Heydari, Akbar
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- Mechanochemical Activation of Iron Cyano Complexes: A Prebiotic Impact Scenario for the Synthesis of α-Amino Acid Derivatives
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Mechanochemical activation of iron cyano complexes by ball milling results in the formation of HCN, which can be trapped and incorporated into α-aminonitriles. This prebiotic impact scenario can be extended by mechanochemically transforming the resulting α-aminonitriles into α-amino amides using a chemical route related to early Earth conditions.
- Bolm, Carsten,Mocci, Rita,Schumacher, Christian,Turberg, Mathias,Puccetti, Francesco,Hernández, José G.
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supporting information
p. 2423 - 2426
(2018/02/09)
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- Synthesis of novel α-amidino carboxylic acids and their use as h-bond catalysts in strecker reaction
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Aim and Objective: A wide variety of synthesized amidine derivatives are bioactive compounds. They show a vast range of medical properties. Therefore, a simple route for synthesis of novel class of amidine derivatives called amidino carboxylic acids and their use as catalysts in Strecker reaction has been reported in the current work. The stability, local charge density and hydrogen bond parameters were calculated for eight derivatives with different substituents. Materials and Methods: In order to synthesize these amidino carboxylic acids, we initially prepared Knovenogel condensation products via the reaction of isatin derivatives with malonitrile. When the reaction was performed in water, the resulting nitrile groups of malonitrile derivatives was hydrolyzed with HOAC/ H2SO4 to generate the desired amide groups. The amide groups in resulting compound converted to amine groups with two Hoffman rearrangements in the presence of NaOH/Br2. Further neutralization led to the final zwitterionic ɑ-amidino carboxylic acids. In the next step, the catalytic activity of these compounds as H-bond donor catalyst was investigated in Strecker reaction. Results: The overall yields of the derivatives with substituent on the aromatic ring of starting isatins are higher than that for the overall yields of nitrogen-substituted isatins. The reaction of 5-nitro isatin with the next reagent gives lower yield in aryl-substituted products. An increase of catalytic activity is observed by rising the electron-withdrawing power of the aromatic ring substituents., The presence of nitro group in the structure of catalyst caused a large increase of catalytic activity in Strecker reaction. DFT calculations at B3LYP/6-31++g(d,p) and Lanl2dz level of theory showed that these compounds act as single H-bond catalysts and higher yields were obtained for complexes with stronger hydrogen bond. Conclusion: A simple and efficient method for synthesis of ɑ-amidino carboxylic acids was developed in this research. These compounds have been used as a single H-bond donor catalyst in the Strecker reaction. DFT calculations were carried out to confirm the experimental results. The obtained data from computations are in good agreement with experimental results.
- Zaghari, Zahra,Azizian, Javad
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p. 609 - 614
(2019/01/14)
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- In(III) and Sc(III) based coordination polymers derived from rigid benzimidazole-5,6-dicarboxylic acid: Synthesis, crystal structure and catalytic property
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Two new coordination polymers (CPs), [InCl(H2bidc)2(H2O)]n (1) and [Sc(Hbidc)(OH)(H2O)]n (2) (H3bidc = benzimidazole-5,6-dicarboxylic acid) were synthesized through a solvotherma
- Chai, Juan,Wang, Pengcheng,Jia, Jia,Ma, Bing,Sun, Jing,Tao, Yufang,Zhang, Ping,Wang, Li,Fan, Yong
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p. 369 - 376
(2017/12/04)
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- An in-based 3D metal-organic framework as heterogeneous Lewis acid catalyst for multi-component Strecker reactions
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A novel three-dimensional metal-organic framework (MOF) {[In3(NIPH)3 (HNIPH)(OH)2]·4H2O}n (1) (H2NIPH = 5-nitroisophthalic acid) with one-dimensional channels was synthesized and structurally characterized. Importantly, it demonstrates excellent catalytic activity for the Strecker reactions of two or three components under mild conditions. Moreover, the catalytic recycling of 1 as a representative example was explored. It can be easily separated and reused for no less than five runs with more than 80% conversion yield in catalytic ability.
- Chai, Juan,Zhang, Ping,Xu, Jianing,Qi, Hui,Sun, Jing,Jing, Shubo,Chen, Xiaodong,Fan, Yong,Wang, Li
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supporting information
p. 165 - 171
(2018/05/07)
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- First Example of a Nonanuclear Silver Sulfate Hybrid Cluster: Green Approach for Synthesis of Lewis Acid Catalyst
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Finding a high nuclearity hybrid framework with novel structure and properties by an environmentally benign approach is a really challenging task. Herein, a green strategy for synthesis of a new inorganic-organic hybrid framework solid has been described. The framework contains silver sulfate clusters with nine different silver ions with shortest silver-silver connectivity. The present compound is the first example of nonanuclear silver sulfate hybrid framework with a new topology. The hybrid solid compound shows a highly active Lewis acidic nature for the various heterogeneous catalytic reactions such as cyanosilylation, ketalization, and esterification with quantitative transformation and recyclability.
- Paul, Avijit Kumar,Naveen, Kumari,Kumar, Nikhil,Kanagaraj, Rajendiran,Vidya,Rom, Tanmay
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p. 6411 - 6416
(2018/11/21)
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- First Example of a Nonanuclear Silver Sulfate Hybrid Cluster: Green Approach for Synthesis of Lewis Acid Catalyst
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Finding a high nuclearity hybrid framework with novel structure and properties by an environmentally benign approach is a really challenging task. Herein, a green strategy for synthesis of a new inorganic-organic hybrid framework solid has been described. The framework contains silver sulfate clusters with nine different silver ions with shortest silver-silver connectivity. The present compound is the first example of nonanuclear silver sulfate hybrid framework with a new topology. The hybrid solid compound shows a highly active Lewis acidic nature for the various heterogeneous catalytic reactions such as cyanosilylation, ketalization, and esterification with quantitative transformation and recyclability.
- Paul, Avijit Kumar,Naveen, Kumari,Kumar, Nikhil,Kanagaraj, Rajendiran,Vidya,Rom, Tanmay
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- Alpha-cyanidation method of mono-alkyl substituted aniline
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The invention discloses an alpha-cyanidation method of mono-alkyl substituted aniline. According to the method, various aromatic, aliphatic, and heterocycle substituted secondary amines of anilines are taken as the raw materials, trimethylsilyl cyanide is
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Paragraph 0021-0101
(2017/09/13)
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- Expeditious and efficient synthesis of Strecker's α-aminonitriles catalyzed by sulfated polyborate
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A straightforward, mild, efficient, and environmentally benign protocol for a three-component Strecker reaction of aldehydes or ketones, amines, and trimethylsilyl cyanide catalyzed by sulfated polyborate has been described to afford α-aminonitriles under solvent-free reaction conditions. The major advantages of the present method are excellent yields, shorter reaction time, simple experimental procedure, easy workup procedure, recyclability of the catalyst, solvent-free reaction conditions and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards.
- Indalkar, Krishna S.,Khatri, Chetan K.,Chaturbhuj, Ganesh U.
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supporting information
p. 2144 - 2148
(2017/05/10)
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- Chiral Cadmium(II) Metal-Organic Framework from an Achiral Ligand by Spontaneous Resolution: An Efficient Heterogeneous Catalyst for the Strecker Reaction of Ketones
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A thermally stable cadmium-based chiral metal-organic framework (MOF), {[Cd2(L)(H2O)(DMF)]·3DMF·2H2O}n (1; DMF = N,N-dimethylformamide), has been synthesized from an achiral ligand by spontaneous resolution. The MOF features 1D open channels with a large density of active metal sites and has a 3,6-c binodal net with a rare sit 3,6-conn topology. The metal-bound water and DMF solvents could be easily removed along with the guest molecules in the lattice upon activation to afford the desolvated framework 1′. It exhibits microporous nature, as confirmed by the gas-sorption measurements with carbon dioxide uptake of 43.2 cm3 g-1 at 273 K. The open metal sites in the framework make it an outstanding heterogeneous catalyst in the Strecker reaction for the synthesis of α-aminonitriles in a solvent-free state at room temperature with excellent conversion yields.
- Verma, Ashish,Tomar, Kapil,Bharadwaj, Parimal K.
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supporting information
p. 13629 - 13633
(2017/11/24)
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- From Zn(II)-Carboxylate to Double-Walled Zn(II)-Carboxylato Phosphate MOF: Change in the Framework Topology, Capture and Conversion of CO2, and Catalysis of Strecker Reaction
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The ligand H2L has been built by linking an imidazole moiety to the 5-position of isophthalic acid. It forms two types of porous frameworks, {[Zn(L)]·2DMF·2H2O}n (1) and {[(CH3)2NH2][Znsub
- Gupta, Mayank,De, Dinesh,Tomar, Kapil,Bharadwaj, Parimal K.
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p. 14605 - 14611
(2017/12/15)
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- Highly efficient three-component Strecker-type reaction catalyzed by MgI2 etherate under solvent-free conditions
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A concise, straightforward and efficient method has been developed for the synthesis of α-aminonitriles by an one-pot three-component condensation of aldehydes or ketones, amines and trimethylsilyl cyanide catalyzed by MgI2 etherate under solvent-free conditions. This protocol has some advantages such as mild reaction condition, simple work-up, short reaction time and high product yields.
- Li, Pengcheng,Zhang, Yongdong,Chen, Zhili,Zhang, Xingxian
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supporting information
p. 1854 - 1858
(2017/04/21)
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- Synthesis of novel magnetic nanoparticles with urea or urethane moieties: Applications as catalysts in the Strecker synthesis of α-aminonitriles
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Four novel magnetic nanoparticle catalysts with urea or urethane moieties are reported. The silica-coated magnetic nanoparticles were simply functionalized via addition of 3-(triethoxysilyl)propylisocyanate (TESPIC), amine or amino alcohol. TESPIC with dual labile functional groups was used as a suitable precursor for the synthesis of urethane-based catalysts. The newly synthesized catalysts were fully characterized using a variety of techniques. These functionalized magnetic nanoparticles were used as reusable catalysts in the Strecker synthesis of α-aminonitrile derivatives under solvent-free conditions at 50?°C.
- Baghery, Saeed,Zolfigol, Mohammad Ali,Schirhagl, Romana,Hasani, Masoumeh,Stuart, Marc C.A.,Nagl, Andreas
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