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Reactivity of secondary N-alkyl acrylamides in Morita–Baylis–Hillman reactions
The Morita–Baylis–Hillman (MBH) reaction of secondary N-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a 1:1 water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary N-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions.
Ahmar, Mohammed,Queneau, Yves,Verrier, Charlie,Yue, Xiaoyang
p. 319 - 330
(2021/10/29)

Ru(ii)- And Ru(iv)-dmso complexes catalyze efficient and selective aqueous-phase nitrile hydration reactions under mild conditions
New water-soluble ruthenium(ii)- and ruthenium(iv)-dmso complexes [RuCl2(dmso)2(NH3)(CH3CN)] (1), [RuCl2(dmso)3(CH3CN)] (2), and [RuCl2(dmso)3(NH3)]·PF6·Cl (3) have been synthesized and characterized using elemental analyses, IR, 1H and 31P NMR, and electronic absorption spectroscopy. The molecular structures of complexes 1-3 were determined crystallographically. The reactivity of complexes 1-3 has been tested for aqueous-phase nitrile hydration at 60 °C in air, and good efficiency and selectivity are shown for the corresponding amide derivatives. Best performance is achieved with complex 3. Amide conversions of 56-99% were obtained with a variety of aromatic, alkyl, and vinyl nitriles. The reaction tolerated hydroxyl, nitro, bromo, formyl, pyridyl, benzyl, alkyl, and olefinic functional groups. Amides were isolated by simple decantation from the aqueous-phase catalyst. A catalyst loading down to 0.0001 mol% was examined and turnover numbers as high as 990?000 were observed. The catalyst was stable for weeks in solution and could be reused more than seven times without significant loss in catalytic activity. The gram-scale reaction was also performed to produce the desired product in high yields. This journal is
Dubey, Santosh Kumar,Kaur, Gurmeet,Rath, Nigam P.,Trivedi, Manoj
p. 17339 - 17346
(2021/10/08)

Simultaneous generation of acrylamide, β-carboline heterocyclic amines and advanced glycation ends products in an aqueous Maillard reaction model system
The simultaneous formation of acrylamide; β-carboline heterocyclic amines (HAs): harmane and norharmane; and advanced glycation end products (AGEs) (Nε-(carboxymethyl)lysine (CML) and Nε-(carboxyethyl)lysine (CEL)) was analyzed based on an aqueous model system. The model systems included lysine–glucose (Lys/Glu), asparagine–glucose (Asn/Glu), tryptophan–glucose (Trp/Glu), and a mixture of these amino acids (Mix/Glu). Only AGEs were generated when heated at 100 °C, Asn and Trp competed with Lys for glucose and methylglyoxal (MGO), and glyoxal (GO) decreased AGE content. The k value of CML, CEL, and acrylamide decreased when heated at 130 °C, whereas that of harmane increased in the Mix/Glu, owing to the competition between Lys and Asn for glucose, GO, and MGO. Harmane preferably formed via the Pictet–Spengler condensation between Trp and acetaldehyde, which further reduced acrylamide formation via the acrolein pathway.
Chen, Jie,He, Zhiyong,Jiao, Ye,Li, Yong,Liu, Guoping,Qin, Fang,Quan, Wei,Wang, Zhaojun,Xue, Chaoyi,Zeng, Maomao
(2020/07/06)

INTEGRATED METHODS AND SYSTEMS FOR PRODUCING AMIDE AND NITRILE COMPOUNDS
Provided herein are integrated methods and systems for the production of acrylamide and acrylonitrile compounds and other compounds from at least beta-lactones and/or beta-hydroxy amides.
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(2020/09/30)

Pyridine-Enabled C-N Bond Activation for the Rapid Construction of Amides and 4-Pyridylglyoxamides by Cooperative Palladium/Copper Catalysis
A pyridine-enabled C-N bond activation of peptidomimetics employing cooperative palladium/copper catalysis in water is developed. Diverse amides and 4-pyridylglyoxamides are simultaneously synthesized through two steps from commercially available materials in a rapid, environmentally friendly, and high atom-economical manner.
Song, Liangliang,Claessen, Sander,Van Der Eycken, Erik V.
p. 8045 - 8054
(2020/07/15)

A Heterogeneous Ruthenium dmso Complex Supported onto Silica Particles as a Recyclable Catalyst for the Efficient Hydration of Nitriles in Aqueous Medium
In the present work, we describe an efficient method for the covalent anchoring of a Ru-dmso complex onto two types of supports: mesoporous silica particles (SP) and silica coated magnetic particles (MSNP). First, we have prepared and characterized the molecular complexes containing the bidentate pyridylpyrazole ligands pypz-Me and pypz-CH2COOEt, with the formula [RuIICl2(pypz-R)(dmso)2] (R = Me, 1; CH2COOEt, 2). Complex 2 was anchored onto the silica supports, yielding the heterogeneous systems SP@2 and MSNP@2 which were fully characterized by IR, UV-vis, SEM, TEM, TGA, and XPS techniques. Hydration of representative nitriles has been tested with the molecular complexes and their SP@2 and MSNP@2 heterogeneous counterparts, in aqueous medium under neutral conditions. The heterogeneous catalysts display high yields and excellent selectivity values. Both systems can be reused throughout several cycles for benzonitrile and acrylonitrile substrates, without any significant loss in reactivity. The MSNP@2 material can be easily recovered by a magnet, facilitating its reusability.
Manrique, Ester,Ferrer, Ingrid,Lu, Changyong,Fontrodona, Xavier,Rodríguez, Montserrat,Romero, Isabel
p. 8460 - 8470
(2019/07/03)

Trash to treasure: Eco-friendly and practical synthesis of amides by nitriles hydrolysis in WepPA
The hydration of nitriles to amides in a water extract of pomelo peel ash (WEPPA) was realized with moderate to excellent yields without using external transition metals, bases or organic solvents. This reaction features a broad substrate scope, wide functional group tolerance, prominent chemoselectivity, and good reusability. Notably, a magnification experiment in this bio-based solvent at 100 mmol further demonstrated its practicability.
Sun, Yajun,Jin, Weiwei,Liu, Chenjiang
supporting information

(2019/11/11)

Pyrrolopyrimidine vs Imidazole-Phenyl-Thiazole Scaffolds in Nonpeptidic Dimerization Inhibitors of Leishmania infantum Trypanothione Reductase
Disruption of protein-protein interactions of essential oligomeric enzymes by small molecules represents a significant challenge. We recently reported some linear and cyclic peptides derived from an α-helical region present in the homodimeric interface of Leishmania infantum trypanothione reductase (Li-TryR) that showed potent effects on both dimerization and redox activity of this essential enzyme. Here, we describe our first steps toward the design of nonpeptidic small-molecule Li-TryR dimerization disruptors using a proteomimetic approach. The pyrrolopyrimidine and the 5-6-5 imidazole-phenyl-thiazole α-helix-mimetic scaffolds were suitably decorated with substituents that could mimic three key residues (K, Q, and I) of the linear peptide prototype (PKIIQSVGIS-Nle-K-Nle). Extensive optimization of previously described synthetic methodologies was required. A library of 15 compounds bearing different hydrophobic alkyl and aromatic substituents was synthesized. The imidazole-phenyl-thiazole-based analogues outperformed the pyrrolopyrimidine-based derivatives in both inhibiting the enzyme and killing extracellular and intracellular parasites in cell culture. The most active imidazole-phenyl-thiazole compounds 3e and 3f inhibit Li-TryR and prevent growth of the parasites at low micromolar concentrations similar to those required by the peptide prototype. The intrinsic fluorescence of these compounds inside the parasites visually demonstrates their good permeability in comparison with previous peptide-based Li-TryR dimerization disruptors.
Revuelto, Alejandro,Ruiz-Santaquiteria, Marta,De Lucio, Héctor,Gamo, Ana,Carriles, Alejandra A.,Gutiérrez, Kilian Jesús,Sánchez-Murcia, Pedro A.,Hermoso, Juan A.,Gago, Federico,Camarasa, María-José,Jiménez-Ruiz, Antonio,Velázquez, Sonsoles
p. 873 - 891
(2019/05/16)

Epicatechin Adducting with 5-Hydroxymethylfurfural as an Inhibitory Mechanism against Acrylamide Formation in Maillard Reactions
This study aimed to investigate the inhibitory mechanism of epicatechin (EC) on the formation of acrylamide in Maillard reactions. The glucose + asparagine model is a typical chemical system used to investigate acrylamide formation. 5-Hydroxymethylfurfural (HMF) is an important carbonyl intermediate in Maillard reactions and can also react with asparagine to form acrylamide. Time courses showed that EC inhibited more HMF than acrylamide in the glucose + asparagine model heated at 180 °C. The reduction of EC on acrylamide formation in the HMF + asparagine model was about 70%, while that in the glucose + asparagine model was about 50%. Moreover, HMF decreased significantly faster when it was heated in the presence of EC. Liquid chromatography-mass spectrometry analysis revealed the formation of adducts between EC and HMF, and the dimeric adducts were verified in fried potato chips. These results suggested that the condensation of EC and HMF was one of the key steps leading to the inhibition of acrylamide. UV-visible spectra analysis showed that some polymerization products had absorption in the visible region and contributed to the development of browning, which was underestimated in the past.
Qi, Yajing,Zhang, Hui,Zhang, Hao,Wu, Gangcheng,Wang, Li,Qian, Haifeng,Qi, Xiguang
p. 12536 - 12543
(2018/11/25)

Water-soluble superbulky (η6- p -cymene) ruthenium(ii) amine: An active catalyst in the oxidative homocoupling of arylboronic acids and the hydration of organonitriles
A phosphine free water-soluble superbulky amine-ruthenium-arene complex (2) encompassing 2,6-bis(diphenylmethyl)-4-methylaniline was synthesised in good yield. 2 was characterized by FT-IR, 1H NMR, and 13C NMR spectroscopies, TGA and elemental analyses. The structure of 2 was confirmed by a single-crystal X-ray diffraction study. The ruthenium centre in 2 adopts the pseudo-octahedral geometry due to the η6-p-cymene ring and bulky aniline ligand along with two chloro groups. Besides, complex 2 was efficaciously employed as a catalyst in the hydration of organonitriles to amides. This reaction proceeds efficiently for a wide range of substrates in an environmentally benign medium and is an economically reasonable synthetic route to amides in good yields. In addition, 2 acts as an excellent catalyst in the oxidative homocoupling of arylboronic acids in water. A range of arylboronic acids undergo a homocoupling reaction in the presence of catalyst 2 to yield symmetrical biaryls in reasonable to good yields.
Nirmala, Muthukumaran,Adinarayana, Mannem,Ramesh, Karupnaswamy,Maruthupandi, Mannarsamy,Vaddamanu, Moulali,Raju, Gembali,Prabusankar, Ganesan
supporting information
p. 15221 - 15230
(2018/09/29)

Monomeric nickel hydroxide stabilized by a sterically demanding phosphorus-nitrogen PN3P-pincer ligand: synthesis, reactivity and catalysis
A terminal nickel hydroxide complex (PN3P)Ni(OH) (3) bearing the 2nd generation phosphorus-nitrogen PN3P-pincer ligand has been synthesized and structurally characterized. As a nucleophile, 3 reacts with CO to afford the hydroxycarbonyl complex 4, (PN3P)Ni(COOH). 3 can also activate CO2 and CS2 to produce nickel bicarbonate (PN3P)Ni(OCOOH) (5) and bimetallic dithiocarbonate [(PN3P)NiS]2CO (6) respectively, as well as to promote aryl isocyanate and isothiocyanate insertion into the Ni-OH bond to give the corresponding (PN3P)NiEC(O)NHAr complexes (E = O, 7; E = S, 8). In addition, 3 catalyzes the nitrile hydration to various amides with well-defined intermediates (PN3P)Ni-NHC(O)R (R = Me, 9; R = Ph, 10).
Yao, Changguang,Chakraborty, Priyanka,Aresu, Emanuele,Li, Huaifeng,Guan, Chao,Zhou, Chunhui,Liang, Lan-Chang,Huang, Kuo-Wei
p. 16057 - 16065
(2018/11/30)

Analyzing the function of the insert region found between the α and β-subunits in the eukaryotic nitrile hydratase from Monosiga brevicollis
The functional roles of the (His)17 region and an insert region in the eukaryotic nitrile hydratase (NHase, EC 4.2.1.84) from Monosiga brevicollis (MbNHase), were examined. Two deletion mutants, MbNHaseΔ238?257 and MbNHaseΔ219?272, were prepared in which the (His)17 sequence and the entire insert region were removed. Each of these MbNHase enzymes provided an α2β2 heterotetramer, identical to that observed for prokaryotic NHases and contains their full complement of cobalt ions. Deletion of the (His)17 motif provides an MbNHase enzyme that is ～55% as active as the WT enzyme when expressed in the absence of the Co-type activator (ε) protein from Pseudonocardia thermophila JCM 3095 (PtNHaseact) but ～28% more active when expressed in the presence of PtNHaseact. MbNHaseΔ219?272 exhibits ～55% and ～89% of WT activity, respectively, when expressed in the absence or presence of PtNHaseact. Proteolytic cleavage of MbNHase provides an α2β2 heterotetramer that is modestly more active compared to WT MbNHase (kcat = 163 ± 4 vs 131 ± 3 s?1). Combination of these data establish that neither the (His)17 nor the insert region are required for metallocentre assembly and maturation, suggesting that Co-type eukaryotic NHases utilize a different mechanism for metal ion incorporation and post-translational activation compared to prokaryotic NHases.
Yang, Xinhang,Bennett, Brian,Holz, Richard C.
p. 1 - 7
(2018/09/18)

Photoiodocarboxylation of Activated C=C Double Bonds with CO2 and Lithium Iodide
The photolysis at 254 nm of lithium iodide and olefins 1 carrying an electron-withdrawing Z-substituent in CO2-saturated (1 bar) anhydrous acetonitrile at room temperature produces the atom efficient and transition metal-free photoiodocarboxylation of the C=C double bond. The reaction proceeds well for terminal olefins 1 to form the new C-I and C-C σ-bonds at the α and β-positions of the Z-substituent, respectively, and is strongly inhibited by polar protic solvents or additives. The experimental results suggest that the reaction channels through the radical anion [CO2?-] in acetonitrile, yet involves different intermediates in aqueous medium. The stabilizing ion-quadrupole and electron donor-acceptor interactions of CO2 with the iodide anion play a crucial role in the reaction course as they allow CO2 to penetrate the solvation shell of the anion in acetonitrile, but not in water. The reaction paths and the reactive intermediates involved under different conditions are discussed.
Mello, Rossella,Arango-Daza, Juan Camilo,Varea, Teresa,González-Nú?ez, María Elena
p. 13381 - 13394
(2018/11/20)

Study on the degradation mechanism and pathway of benzene dye intermediate 4-methoxy-2-nitroaniline: Via multiple methods in Fenton oxidation process
Benzene dye intermediate (BDI) 4-methoxy-2-nitroaniline (4M2NA) wastewater has caused significant environmental concern due to its strong toxicity and potential carcinogenic effects. Reports concerning the degradation of 4M2NA by advanced oxidation process are limited. In this study, 4M2NA degradation by Fenton oxidation has been studied to obtain more insights into the reaction mechanism involved in the oxidation of 4M2NA. Results showed that when the 4M2NA (100 mg L-1) was completely decomposed, the TOC removal efficiency was only 30.70-31.54%, suggesting that some by-products highly recalcitrant to the Fenton oxidation were produced. UV-Vis spectra analysis based on Gauss peak fitting, HPLC analysis combined with two-dimensional correlation spectroscopy and GC-MS detection were carried out to clarify the degradation mechanism and pathway of 4M2NA. A total of nineteen reaction intermediates were identified and two possible degradation pathways were illustrated. Theoretical TOC calculated based on the concentration of oxalic acid, acetic acid, formic acid, and 4M2NA in the degradation process was nearly 94.41-97.11% of the measured TOC, indicating that the oxalic acid, acetic acid and formic acid were the main products. Finally, the predominant degradation pathway was proposed. These results could provide significant information to better understand the degradation mechanism of 4M2NA.
Guo, Ying,Xue, Qiang,Cui, Kangping,Zhang, Jia,Wang, Hui,Zhang, Huanzhen,Yuan, Fang,Chen, Honghan
p. 10764 - 10775
(2018/03/26)

Hemilability-Driven Water Activation: A NiII Catalyst for Base-Free Hydration of Nitriles to Amides
The NiII complex 1 containing pyridyl- and hydroxy-functionalized N-heterocyclic carbenes (NHCs) is synthesized and its catalytic utility for the selective nitrile hydration to the corresponding amide under base-free conditions is evaluated. The title compound exploits a hemilabile pyridyl unit to interact with a catalytically relevant water molecule through hydrogen-bonding and promotes a nucleophilic water attack to the nitrile. A wide variety of nitriles is hydrated to the corresponding amides including the pharmaceutical drugs rufinamide, Rifater, and piracetam. Synthetically challenging α-hydroxyamides are accessed from cyanohydrins under neutral conditions. Related catalysts that lack the pyridyl unit (i.e., compounds 2 and 4) are not active whereas those containing both the pyridyl and the hydroxy or only the pyridyl pendant (i.e., compounds 1 and 3) show substantial activity. The linkage isomer 1′ where the hydroxy group is bound to the metal instead of the pyridyl group was isolated under different crystallization conditions insinuating a ligand hemilabile behavior. Additional pKa measurements reveal an accessible pyridyl unit under the catalytic conditions. Kinetic studies support a ligand-promoted nucleophilic water addition to a metal-bound nitrile group. This work reports a Ni-based catalyst that exhibits functional hemilability for hydration chemistry.
Singh, Kuldeep,Sarbajna, Abir,Dutta, Indranil,Pandey, Pragati,Bera, Jitendra K.
p. 7761 - 7771
(2017/06/06)

Controlled photocatalytic hydrolysis of nitriles to amides by mesoporous MnO2 nanoparticles fabricated by mixed surfactant mediated approach
The solid-phase MnO2 nanoparticles fabricated by surfactant template method were exploited as the photocatalyst for the effective one-step synthesis of amides. Cationic or anionic surfactants and their combinations were used as porous templates to obtain the mesoporous MnO2 nanoparticles with variable pore volume (0.23–1.95?cm3/g). The morphological and structural observation of the material confirms the uniform facet structure (37.68?nm) of MnO2 nanoparticles. The surface elemental state was confirmed by XPS analysis confirming Mn 2p3/2 (642.5?eV) and Mn2p1/2 (654.7?eV) spin states, that are common for the tetravalent Mn ions. Presence of surfactant as stabilizer was also witnessed with a strong peak of C 1s (283–286?eV). The textural parameters obtained from XRD and Raman analysis depicted the β-phase and rutile type framework of MnO2. The selective conversion of nitriles to amides was studied without any acid by products under visible light irradiation in the basic/neutral medium. Amides were obtained from various substrates (nitriles) with excellent yields (70–90%).
Mehta, Akansha,Basu, Soumen
p. 1 - 6
(2017/04/24)

METHOD FOR REFINING AMIDE COMPOUND, AND AMIDE COMPOUND REFINING DEVICE
PROBLEM TO BE SOLVED: To provide a method for efficiently refining an amide compound produced by the hydration reaction of a nitryl compound using an amide compound-containing liquid, particularly, its bacterial cell and/or bacterial cell treated product thereof as a catalyst. SOLUTION: Provided is a method for refining an amide compound characterized in that, in a method for refining an amide compound produced using a nitrile-hydratase-containing bacterial cell and/or its bacterial cell treated product, an amide compound-containing liquid after refining treatment is mixed with a neutralizer and is thereafter fed to a neutralization tank. Also provided is an amide compound refining device comprising: a neutralization tank for neutralizing the refined liquid of an amide compound produced using a nitrile-hydratase-containing bacterial cell and/or its bacterial cell treated product; and a feed line for feeding a mixture of the amide compound-containing liquid and a neutralizer. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT
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(2017/09/12)

Biomimetic-functionalized, tannic acid-templated mesoporous silica as a new support for immobilization of nhase
Tannic acid-templated mesoporous silica (TAMS) was synthesized using a simple nonsurfactant template method and dopamine-functionalized TAMS (Dop-TAMS), which was prepared via a biomimetic coating, was developed as a new support for immobilization of NHase (NHase@Dop-TAMS). The Dop-TAMS was thoroughly characterized by the transmission electron microscopy (TEM), scanning electron microscopy (SEM), Brunauer–Emmett–Teller (BET), and Fourier transform infrared (FT-IR) and the results showed that the Dop-TAMS possessed sufficiently large pore size and volume for the accommodation of NHase. Studying the thermal stability, storage, shaking stability, and pH stability of the free and immobilized NHase indicated that the catalytic properties of NHase@Dop-TAMS were significantly enhanced. Moreover, the NHase@Dop-TAMS exhibited good reusability. All the results demonstrated that Dop-TAMS could be used as an excellent matrix for the immobilization of NHase.
Gao, Jun-kai,Zhang, Zi-jun,Jiang, Yan-jun,Chen, Yan,Gao, Shu-feng
(2017/10/13)

Preparation method of acrylamide-based compounds
The present invention relates to the field of fine chemical materials, particularly to a new mild, efficient and economical preparation process technology of a class of acrylamide-type compounds, wherein a beta-amine substituted propionamide precursor is subjected to an in-situ amine elimination reaction under the action of a suitable electrophilic reagent so as to prepare the target product.
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(2018/01/11)

α,β-UNSATURATED CARBOXYLIC ACID SUCH AS ACRYLIC ACID, MANUFACTURING METHOD OF DERIVATIVE THEREOF
PROBLEM TO BE SOLVED: To provide a manufacturing method of selectively synthesizing α,β-unsaturated carboxylic acid or a derivative thereof with yield (yield of about 40% or more) and selectivity equal to or more than those of conventional techniques by a high temperature and high pressure treated water treatment from 2-hydroxy carboxylic acid or a derivative thereof. SOLUTION: In a reaction for obtaining α,β-unsaturated carboxylic acid and/or a derivative thereof from 2-hydroxycarboxylic acid and/or a derivative thereof, they are reacted in presence of a metal, excluding austenite stainless steel, a nickel chromium molybdenum alloy, a nickel chromium iron niobium alloy and brass, in high temperature and high pressure water of 200°C to 500°C and 10 MPa to 50 MPa. SELECTED DRAWING: Figure 5 COPYRIGHT: (C)2017,JPOandINPIT
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(2017/12/27)

Poly(amic acid) salt-stabilized silver nanoparticles as efficient and recyclable quasi-homogeneous catalysts for the aqueous hydration of nitriles to amides
Water-soluble silver nanoparticles stabilized by poly(amic acid) salt (Ag-PAAS) were synthesized by a one-pot method and were characterized by using UV-vis absorption, transmission electron microscopy, powder X-ray diffraction, and ζ potential measurements. The Ag-PAAS catalyzed selective hydration of nitriles to amides in water allowed for not only highly efficient quasi-homogeneous catalytic reactions under mild conditions, but also an easy recovery and reuse of the catalyst attributed to the pH response of the PAAS.
Li, Jun,Tang, Guannan,Wang, Yuchen,Wang, Ya,Li, Zixi,Li, Hengfeng
p. 358 - 364
(2016/01/12)

Silica-sulfuric acid: Novel, simple, efficient and reusable catalyst for hydration of nitrile to amide
Silica-sulfuric acid efficiently catalyzes conversion of aliphatic, substituted aromatic and hetero aromatic nitriles to their corresponding amides in good to excellent yields under reflux condition. Products obtained were purified by column chromatography method and characterized by 1H NMR, 13C NMR and mass spectral analysis.
Chandrashekharappa, Sandeep,Venugopala, Katharigatta N.,Venugopala, Rashmi,Odhav, Bharti
p. 2177 - 2180
(2016/07/21)

Bis(allyl)-ruthenium(IV) complexes with phosphinous acid ligands as catalysts for nitrile hydration reactions
Several mononuclear ruthenium(iv) complexes with phosphinous acid ligands [RuCl2(η3:η3-C10H16)(PR2OH)] have been synthesized (78-86% yield) by treatment of the dimeric precursor [{RuCl(μ-Cl)(η3:η3-C10H16)}2] (C10H16 = 2,7-dimethylocta-2,6-diene-1,8-diyl) with 2 equivalents of different aromatic, heteroaromatic and aliphatic secondary phosphine oxides R2P(O)H. The compounds [RuCl2(η3:η3-C10H16)(PR2OH)] could also be prepared, in similar yields, by hydrolysis of the P-Cl bond in the corresponding chlorophosphine-Ru(iv) derivatives [RuCl2(η3:η3-C10H16)(PR2Cl)]. In addition to NMR and IR data, the X-ray crystal structures of representative examples are discussed. Moreover, the catalytic behaviour of complexes [RuCl2(η3:η3-C10H16)(PR2OH)] has been investigated for the selective hydration of organonitriles in water. The best results were achieved with the complex [RuCl2(η3:η3-C10H16)(PMe2OH)], which proved to be active under mild conditions (60 °C), with low metal loadings (1 mol%), and showing good functional group tolerance.
Tomás-Mendivil, Eder,Francos, Javier,González-Fernández, Rebeca,González-Liste, Pedro J.,Borge, Javier,Cadierno, Victorio
p. 13590 - 13603
(2016/09/04)

MANUFACTURING METHOD OF AMIDE COMPOUND, ALLOY PARTICLE AND CATALYST CONTAINING THE SAME
PROBLEM TO BE SOLVED: To provide an alloy particle for a catalyst capable of manufacturing an amide compound with high efficiency and capable of manufacturing the amide compound at low cost easily on an industrial scale. SOLUTION: There is provided an alloy particle for catalyst used in manufacturing an amide compound having a B2 type or L12 type crystal structure constituted by Cu and Pd or a L10 type crystal structure constituted by Cu and Au and having average particle diameter of the alloy particle of 1 to 200 nm. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2016,JPO&INPIT
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(2017/03/23)

Ru(ii)-dmso complexes containing azole-based ligands: Synthesis, linkage isomerism and catalytic behaviour
The reaction of cis,fac-[RuCl2(dmso-S)3(dmso-O)], 1, with different azole (L) ligands leads to new [RuCl2(L)(dmso-S)3] compounds (L = CH3-pz-H, 2; NO2-pz-H, 3; CF3-pz-H, 4 and Br-Hind, 5). Complexes 2-5 have been characterized by analytical, spectroscopic and electrochemical techniques as well as by monocrystal X-ray diffraction analysis. Upon oxidation to Ru(iii) the complexes undergo linkage isomerization of a S-bound dmso ligand and the corresponding kinetic rates as well as the thermodynamic properties have been determined for compound 2 and also for the previously described [RuIICl2(pypz-H)(dmso-S)2] (pypz-H = 2-(3-pyrazolyl)pyridine), 6, from cyclic voltammetries performed at different scan rates. The exposure of compound 2 to visible light in acetonitrile produces the substitution of one dmso ligand by a solvent molecule generating a new compound, 2′. The irradiation of solutions of compounds 2 and 6 in chloroform leads in both cases to the substitution of one dmso by a chlorido ligand in parallel to the oxidation of Ru(ii) to Ru(iii) generating complexes 2′′ and 6′ respectively. The reactivity of compounds 2-6 has been tested with regard to the hydration of nitriles in water as a solvent, displaying in all cases good performance and selectivity for the corresponding amides.
Ferrer, íngrid,Fontrodona, Xavier,Rodríguez, Montserrat,Romero, Isabel
p. 3163 - 3174
(2016/02/19)

Synthesis of and catalytic nitrile hydration by a cationic tris(μ-hydroxo)diruthenium(II) complex having PMe3ligands
While phenyl vinyl ether does not react with [Ru(η4-1,5-COD)(η6-1,3,5-COT)] (1)/PMe3, the C–O bond cleavage of phenyl vinyl ether occurs by 1/PMe3in the presence of water to give a tris(μ-hydroxo)diruthenium(II) complex [(Me3P)3Ru(μ-OH)3Ru(PMe3)3]+[OPh]?·HOPh (3·HOPh) with evolution of ethylene. The molecular structure of 3·HOPh is unequivocally determined by X-ray analysis. The most likely mechanism for the formation of 3·HOPh is protonation of [Ru(η4-1,5-COD)(PMe3)3] (2c) by water and subsequent insertion of phenyl vinyl ether into the resulting Ru–H bond followed by the β-phenoxide elimination and hydrolysis and dimerization of the phenoxoruthenium(II) species. Complex 3 acts as a catalyst for nitrile hydration. As a typical example, the hydration of benzonitrile was achieved by 3 (1.0 mol%) in 1,4-dioxane at 120 °C for 6 h to give benzamide quantitatively.
Kiyota, Sayori,Kobori, Takako,Soeta, Hirofumi,Ichikawa, You-ichi,Komine, Nobuyuki,Komiya, Sanshiro,Hirano, Masafumi
p. 3 - 10
(2016/12/06)

Ruthenium(II) complexes incorporating salicylaldiminato-functionalized N-heterocyclic carbene ligands as efficient and versatile catalysts for hydration of organonitriles
We describe a new synthetic procedure for synthesis of ruthenium(II) complexes containing salicylaldiminato functionalized mixed N-heterocyclic carbene (NHC) ligand and phosphine co-ligand. The complexes (3a-3d) have been obtained in good to excellent yields by transmetalation from the corresponding Ag-NHC complexes (2a-2d) as carbene transfer reagents. All the [Ru-NHC] complexes have been characterized by elemental analyses, spectroscopic methods as well as ESI mass spectrometry. The ligands 1a-1d show their versatility by switching to be O,N,C-chelating in these ruthenium(II) complexes. The resulting complexes have been evaluated as potential catalysts for the selective hydration of nitriles to primary amides, and related amide bond forming reactions, in environmentally friendly medium. The reaction tolerated ether, hydroxyl, nitro, bromo, formyl, pyridyl, benzyl and alkyl functional groups. The catalyst was stable for weeks and could be recovered and reused more than six times without significant loss of activity.
Nirmala, Muthukumaran,Saranya, Gandhi,Viswanathamurthi, Periasamy
p. 134 - 144
(2016/01/09)

MEANS AND METHODS FOR PRODUCING AMIDE COMPOUNDS WITH LESS ACRYLIC ACID
The present invention relates to means and methods for producing an amide compound from a nitrile compound with less acrylic acid as by-product using a Nitrile hydratase (NHase) and Amidase producing microorganism as biocatalyst. Also provided is an aqueous amide compound obtained by the methods of the invention as well as a composition comprising acrylamide or polyacrylamide as well as a dried microorganism exhibiting a NHase/Amidase activity ratio of at least 400 when being brought into contact with a nitrile compound to convert said nitrile compound into an amide compound.
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(2016/04/26)

Method for producing amide compound
The invention pertains to a technique for suppressing a decrease in nitrile hydratase activity and improving the productivity of the amide compound in the course of producing an amide compound from a nitrile compound using a biocatalyst. Specifically, the invention pertains to a method for producing the corresponding amide compound from a nitrile compound in the presence of a biocatalyst having nitrile hydratase activity, wherein the method for producing an amide compound using a nitrile compound is characterized in that the zinc concentration of the nitrile compound is 0.4 ppm or less.
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(2016/08/07)

DJ-1 family Maillard deglycases prevent acrylamide formation
The presence of acrylamide in food is a worldwide concern because it is carcinogenic, reprotoxic and neurotoxic. Acrylamide is generated in the Maillard reaction via condensation of reducing sugars and glyoxals arising from their decomposition, with asparagine, the amino acid forming the backbone of the acrylamide molecule. We reported recently the discovery of the Maillard deglycases (DJ-1/Park7 and its prokaryotic homologs) which degrade Maillard adducts formed between glyoxals and lysine or arginine amino groups, and prevent glycation damage in proteins. Here, we show that these deglycases prevent acrylamide formation, likely by degrading asparagine/glyoxal Maillard adducts. We also report the discovery of a deglycase from the hyperthermophilic archaea Pyrococcus furiosus, which prevents acrylamide formation at 100?°C. Thus, Maillard deglycases constitute a unique enzymatic method to prevent acrylamide formation in food without depleting the components (asparagine and sugars) responsible for its formation.
Richarme, Gilbert,Marguet, Evelyne,Forterre, Patrick,Ishino, Sonoko,Ishino, Yoshizumi
p. 1111 - 1116
(2016/11/05)

Chemoselective hydration of nitriles to amides using hydrated ionic liquid (IL) tetrabutylammonium hydroxide (TBAH) as a green catalyst
A transition metal-free process, catalyzed by tetrabutylammonium hydroxide (TBAH), has been developed for the convenient and selective hydration of nitriles to the corresponding amides. The present process converts aromatic, aliphatic, and heteroaromatic nitriles with a wide variety of functional groups into amides. The regioselective hydration of one nitrile moiety in the presence of another nitrile group gives the present protocol high impact.
Veisi, Hojat,Maleki, Behrooz,Hamelian, Mona,Ashrafi, Samaneh Sedigh
p. 6365 - 6371
(2015/02/19)

Hydration of nitriles to amides by a chitin-supported ruthenium catalyst
Chitin-supported ruthenium (Ru/chitin) promotes the hydration of nitriles to carboxamides under aqueous conditions. The nitrile hydration can be performed on a gram-scale and is compatible with the presence of various functional groups including olefins, aldehydes, carboxylic esters and nitro and benzyloxycarbonyl groups. The Ru/chitin catalyst is easily prepared from commercially available chitin, ruthenium(III) chloride and sodium borohydride. Analysis of Ru/chitin by high-resolution transmission electron microscopy indicates the presence of ruthenium nanoparticles on the chitin support.
Matsuoka, Aki,Isogawa, Takahiro,Morioka, Yuna,Knappett, Benjamin R.,Wheatley, Andrew E. H.,Saito, Susumu,Naka, Hiroshi
p. 12152 - 12160
(2015/02/19)

Selective hydration of nitriles to amides catalysed by PCP pincer supported nickel(ii) complexes
The (PCP)Ni-OH complexes 2R (R = iPr, tBu, Cy) are effective catalyst precursors for the selective hydration of nitriles to the corresponding amides under relatively mild conditions (80 °C) and low catalyst loadings (0.05-0.5%). Substrate scope includes aliphatic, vinylic and aromatic nitriles, but substrates with protic groups poison the catalyst abruptly. The catalysts are effective because the electron rich nature of the PCP ligands and their steric bulk renders the hydroxo group labile.
Borau-Garcia,Gutsulyak,Burford,Piers
p. 12082 - 12085
(2016/01/15)

Water soluble diphosphine ligands based on 1,3,5-triaza-7-phosphaadamantane (PTA-PR2): Synthesis, coordination chemistry, and ruthenium catalyzed nitrile hydration
Two chiral chelating 1,3,5-triaza-7-phosphaadamantane (PTA) derivatives were synthesized, in racemic form, by addition of ClPiPr2 or ClP(NiPr)2(CH2)2 to lithiated PTA. PTA-PiPr2 (1) and PTA-P(NiPr)2(CH2)2 (2) were isolated in good yield, 73% and 56% respectively, and fully characterized by multinuclear NMR spectroscopy, mass spectrometry, and X-ray crystallography. PTA-PiPr2 is highly air sensitive, but stable and somewhat soluble in degassed water. PTA-P(NiPr)2(CH2)2 (2) is air-stable, but decomposes in water over the course of hours. Two tungsten tetracarbonyl complexes were prepared by addition of the PTA-PR2 to [W(CO)4(pip)2] and characterized by NMR and IR spectroscopies and X-ray crystallography in the case of [W(CO)4(PTA-PiPr2)]. Based on IR spectroscopy PTA-PiPr2 (1) is more electron donating than PTA-P(NiPr)2(CH2)2 (2) or the previously published PTA-PPh2. Products isolated from the reaction of [(η6-toluene)RuCl2]2 with two equivalents of 1 were found to contain monodentate (κ1), bidentate (κ2), and possibly bridging coordination modes of PTA-PiPr2. These ruthenium complexes were explored as catalysts for aqueous phase nitrile hydration. Of the ruthenium complexes explored [(η6-toluene)RuCl2(κ1-PTA-PiPr2)] (7) was the most active towards nitrile hydration. In the presence of air at 100°C 7 converted various nitriles to the respective amides with 43-99% conversions in 7 h.
Sears, Jeremiah M.,Lee, Wei-Chih,Frost, Brian J.
supporting information
p. 248 - 257
(2015/06/02)

Analyzing the catalytic role of active site residues in the Fe-type nitrile hydratase from Comamonas testosteroni Ni1
Abstract A strictly conserved active site arginine residue (αR157) and two histidine residues (αH80 and αH81) located near the active site of the Fe-type nitrile hydratase from Comamonas testosteroni Ni1 (CtNHase), were mutated. These mutant enzymes were examined for their ability to bind iron and hydrate acrylonitrile. For the αR157A mutant, the residual activity (k cat = 10 ± 2 s-1) accounts for less than 1 % of the wild-type activity (k cat = 1100 ± 30 s-1) while the K m value is nearly unchanged at 205 ± 10 mM. On the other hand, mutation of the active site pocket αH80 and αH81 residues to alanine resulted in enzymes with k cat values of 220 ± 40 and 77 ± 13 s-1, respectively, and K m values of 187 ± 11 and 179 ± 18 mM. The double mutant (αH80A/αH81A) was also prepared and provided an enzyme with a k cat value of 132 ± 3 s-1 and a K m value of 213 ± 61 mM. These data indicate that all three residues are catalytically important, but not essential. X-ray crystal structures of the αH80A/αH81A, αH80W/αH81W, and αR157A mutant CtNHase enzymes were solved to 2.0, 2.8, and 2.5 ? resolutions, respectively. In each mutant enzyme, hydrogen-bonding interactions crucial for the catalytic function of the αCys104-SOH ligand are disrupted. Disruption of these hydrogen bonding interactions likely alters the nucleophilicity of the sulfenic acid oxygen and the Lewis acidity of the active site Fe(III) ion.
Martinez, Salette,Wu, Rui,Krzywda, Karoline,Opalka, Veronika,Chan, Hei,Liu, Dali,Holz, Richard C.
p. 885 - 894
(2015/06/30)

Nitrile hydration to amide in water: Palladium-based nanoparticles vs molecular catalyst
The catalytic performance of small Pd-nanoparticles (NPs) (2.0 nm), partially covered by chemisorbed oxygen atoms, and of Pd-acetate, both stabilized by 2,2′-bipyridine-end functionalized poly(ethyleneglycol) monomethylether was compared in the selective hydration of nitriles to amide in water under mild reaction conditions (353 K). Regardless of the nitrile substrate employed, the Pd-NP-based catalyst showed much higher normalized TON-values (i.e. refereeing to the amount of surface Pd atoms) compared to the Pd(II) macrocomplex, as far as the first catalytic run was considered. Deactivation of the Pd-NP-based catalyst was significant due to the formation of a hydroxide-water layer on the NPs' surface.
Oberhauser,Bartoli, Mattia,Petrucci, Giorgio,Bandelli, Damiano,Frediani, Marco,Capozzoli, Laura,Cepek, Cinzia,Bhardwaj, Sunil,Rosi, Luca
p. 26 - 33
(2015/09/28)

Hydration of Nitriles to Amides by Thiolate-Bridged Diiron Complexes
A series of nitrile-coordinating complexes [CpFe(μ-SEt)RCN]2[PF6]2 (1, R = alkyl, aryl, vinyl, amine) have been obtained by the reaction of [CpFe(μ-SEt)MeCN]2[PF6]2 (1a) with various nitriles in acetone. Complexes 1 can realize the hydration of a nitrile ligand under ambient conditions. Complexes [CpFe(μ-SEt)2(μ-η1:η1-NH(O)CR)FeCp][PF6] (2) were successfully isolated as intermediates during the hydration process, with 2b and 2e (R = CH2i = CH and Et2N) being characterized by spectrometry and X-ray crystallography. Treatment of 2 with HBF4·Et2O in the presence of nitriles released corresponding amides 3. At the same time, the structural features of the [Fe2S2] scaffold were retained. These results confirmed that the hydration of nitriles was realized by cooperative interaction on diiron centers. (Figure Presented).
Tong, Peng,Yang, Dawei,Li, Yang,Wang, Baomin,Qu, Jingping
p. 3571 - 3576
(2015/08/06)

Metal complex compound and process for producing amides utilizing the metal complex compound
A catalyst contains a metal complex compound represented by the following general formula (I). In the formula (I), M is a metal ion such as ruthenium, L1 is a cyclic or acyclic, neutral or minus 1-valent unsaturated hydrocarbon group of 1 to 30 carbon atoms which may have a substituent, L2 and L3 are each independently chlorine or the like, and L4 is a compound bonded to M through phosphorus or arsenic and represented by the following general formula (IIa) or (IIb). In the formulas (IIa) and (IIb), E is phosphorus or arsenic, Y1 is oxygen or sulfur, Y2, Y3 and Y4 are each independently a hydrogen atom, an aryl group or the like, and H is a hydrogen atom.
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(2014/05/20)

Mild and selective heterogeneous catalytic hydration of nitriles to amides by flowing through manganese dioxide
A sustainable flow chemistry process for the hydration of nitriles, whereby an aqueous solution of the nitrile is passed through a column containing commercially available amorphous manganese dioxide, has been developed. The product is obtained simply by concentration of the output stream without any other workup steps. The protocol described is rapid, robust, reliable, and scalable, and it has been applied to a broad range of substrates, showing a high level of chemical tolerance.
Battilocchio, Claudio,Hawkins, Joel M.,Ley, Steven V.
supporting information
p. 1060 - 1063
(2016/10/17)

Choline chloride based eutectic solvent: An efficient and reusable solvent system for the synthesis of primary amides from aldehydes and from nitriles
Choline chloride: a 2ZnCl2 based deep eutectic solvent was found to be a simple, green, efficient and new solvent system for the preparation of primary amides from aldehydes. The same catalytic system is also applicable for the preparation of amides from nitriles. Good to excellent yields of primary amides were obtained in both these transformations.
Patil, Umakant B.,Singh, Abhilash S.,Nagarkar, Jayashree M.
p. 1102 - 1106
(2014/01/06)

Acrylamide production using encapsulated nitrile hydratase from Pseudonocardia thermophila in a sol-gel matrix
The cobalt-type nitrile hydratase from Pseudonocardia thermophila JCM 3095 (PtNHase) was successfully encapsulated in tetramethyl orthosilicate sol-gel matrices to produce a PtNHase:sol-gel biomaterial. The PtNHase:sol-gel biomaterial catalyzed the conversion of 600 mM acrylonitrile to acrylamide in 60 min at 35 C with a yields of >90%. Treatment of the biomaterial with proteases confirmed that the catalytic activity is due to the encapsulated enzyme and not surface bound NHase. The biomaterial retained 50% of its activity after being used for a total of 13 consecutive reactions for the conversion of acrylonitrile to acrylamide. The thermostability and long-term storage of the PtNHase:sol-gel are substantially improved compared to the soluble NHase. Additionally, the biomaterial is significantly more stable at high concentrations of methanol (50% and 70%, v/v) as a co-solvent for the hydration of acrylonitrile than native PtNHase. These data indicate that PtNHase:sol-gel biomaterials can be used to develop new synthetic avenues involving nitriles as starting materials given that the conversion of the nitrile moiety to the corresponding amide occurs under mild temperature and pH conditions.
Martinez, Salette,Kuhn, Misty L.,Russell, James T.,Holz, Richard C.,Elgren, Timothy E.
p. 19 - 24
(2014/01/06)

An efficient ruthenium(iv) catalyst for the selective hydration of nitriles to amides in water under mild conditions
A Ru(iv) catalyst able to promote the selective hydration of nitriles to amides in water, at low metal loadings and under mild conditions, is presented. This journal is the Partner Organisations 2014.
Tomás-Mendivil, Eder,Suárez, Francisco J.,Díez, Josefina,Cadierno, Victorio
supporting information
p. 9661 - 9664
(2014/08/18)

Amberlyst A26 OH as a recyclable catalyst for hydration of nitriles and water-based synthesis of 4(1 H)-quinazolinones from 2-aminobenzonitrile and carbonyl compounds
Selective hydration of nitriles to primary amides as well the base-catalyzed synthesis of 2-substituted 4(1H)-quinazolinones via reaction of 2-aminobenzonitrile with carbonyl compounds using macroporous Amberlyst A26 OH in H2O-EtOH is described. The latter reaction proceeds via tandem hydration of 2-aminobenzonitrile, condensation of the in situ generated 2-aminobenzamide with carbonyl compounds, and cyclization of the imine intermediate to give the quinazolinone derivatives. Georg Thieme Verlag Stuttgart New York.
Tamaddon, Fatemeh,Pouramini, Farzaneh
p. 1127 - 1131
(2014/05/20)

Synthesis of glycidamide from acrylonitrile using basic hydrotalcite catalyst in the presence of aqueous hydrogen peroxide and unsaturated amide
Glycidamide (GA) can be synthesized from acrylonitrile (AN) by using hydrotalcite as a solid base catalyst and 25% aqueous H2O2 as an oxidant, in the presence of acrylam ide (AA) as a cocatalyst in methanol solvent at 313K for 18 h. The GA yield and H2O2 utilization efficiency reached 74% and 60%, respectively. The hydrotalcite catalyst could be easily separated from the reaction mixture and reused at least once.
Fujiwara, Shinpei,Nishimura, Shun,Ebitani, Kohki
p. 1716 - 1718
(2015/02/19)

The active site sulfenic acid ligand in nitrile hydratases can function as a nucleophile
Nitrile hydratase (NHase) catalyzes the hydration of nitriles to their corresponding commercially valuable amides at ambient temperatures and physiological pH. Several reaction mechanisms have been proposed for NHase enzymes; however, the source of the nucleophile remains a mystery. Boronic acids have been shown to be potent inhibitors of numerous hydrolytic enzymes due to the open shell of boron, which allows it to expand from a trigonal planar (sp2) form to a tetrahedral form (sp3). Therefore, we examined the inhibition of the Co-type NHase from Pseudonocardia thermophila JCM 3095 (PtNHase) by boronic acids via kinetics and X-ray crystallography. Both 1-butaneboronic acid (BuBA) and phenylboronic acid (PBA) function as potent competitive inhibitors of PtNHase. X-ray crystal structures for BuBA and PBA complexed to PtNHase were solved and refined at 1.5, 1.6, and 1.2 A resolution. The resulting PtNHase-boronic acid complexes represent a "snapshot" of reaction intermediates and implicate the cysteine-sulfenic acid ligand as the catalytic nucleophile, a heretofore unknown role for the αCys113-OH sulfenic acid ligand. Based on these data, a new mechanism of action for the hydration of nitriles by NHase is presented.
Martinez, Salette,Wu, Rui,Sanishvili, Ruslan,Liu, Dali,Holz, Richard
supporting information
p. 1186 - 1189
(2014/02/14)

Magnetically separable and Recyclable Fe3O4-supported Ag Nanocatalysts for reduction of nitro compounds and selective Hydration of Nitriles to Amides in Water
As hybrid nanostructures have become more important in many fields of chemistry, Ag nanoparticles (NPs) are being increasingly immobilized onto Fe3O4 microspheres in situ. Structural characterization reveals that the Ag NPs are uniformly immobilized in the Fe3O 4 microsphere-based supports. Moreover, Ag NPs are more stable in the hybrid structure than in the naked state and show high catalytic activity for the reduction of nitro compounds and hydration of nitriles to amides in water. The Fe3O4 microspheres were recycled several times using an external magnet.
Woo, Hyunje,Lee, Kyoungho,Park, Sungkyun,Park, Kang Hyun
p. 699 - 712
(2014/02/14)

Ag-grafted covalent imine network material for one-pot three-component coupling and hydration of nitriles to amides in aqueous medium
A nitrogen rich porous covalent imine network material (CIN-1) has been successfully employed for grafting silver nanoparticles (Ag NPs). The Ag NPs grafted CIN-1, Ag-CIN-1 has been characterized by elemental analysis, powder X-ray diffraction (XRD), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), UV-vis diffuse reflectance spectroscopy (DRS), thermogravimetric analysis (TGA) and EPR spectroscopic studies. Ag-CIN-1 acts as a truly heterogeneous catalyst in the hydration of nitriles to amides and the A3 coupling reactions between the alkyne, amine and aldehyde to produce propargylamines by using water as a green solvent. This journal is
Salam, Noor,Kundu, Sudipta K.,Molla, Rostam Ali,Mondal, Paramita,Bhaumik, Asim,Islam, Sk. Manirul
p. 47593 - 47604
(2015/02/19)

Poly (N-2-aminoethylacrylamide) grafted polystyrene-Cu (II) complex catalyzed conversion of aldehydes into primary amides in water
Poly (N-2-aminoethylacrylamide) grafted polystyrene-Cu (II) complex was synthesized and characterized by techniques such as FTIR spectroscopy, XRD, SEM-EDX, TGA and ICP-AES analysis. The catalyst exhibits an excellent catalytic activity for the conversion of various aldehydes to corresponding amides in water. Also, the catalyst could be recovered and reused five times without any significant loss in its activity.
Kurhe, Deepak K.,Jayaram, Radha V.
p. 69 - 72
(2014/10/16)

Poly (N-2-aminoethylacrylamide) grafted polystyrene-Cu (II) complex catalyzed conversion of aldehydes into primary amides in water
Poly (N-2-aminoethylacrylamide) grafted polystyrene-Cu (II) complex was synthesized and characterized by techniques such as FTIR spectroscopy, XRD, SEM-EDX, TGA and ICP-AES analysis. The catalyst exhibits an excellent catalytic activity for the conversion of various aldehydes to corresponding amides in water. Also, the catalyst could be recovered and reused five times without any significant loss in its activity.
Kurhe, Deepak K.,Jayaram, Radha V.
p. 69 - 72
(2014/12/11)

NITRILE HYDRATION CATALYZED BY RECYCLABLE RUTHENIUM COMPLEXES
A method for hydrating a nitrile derivative to generate an amide derivative is provided. The method includes mixing the nitrile derivative with a ruthenium catalyst complex in an aqueous solution to form a mixture, and reacting the nitrile derivative with water in the aqueous solution and in the presence of the ruthenium catalyst complex to form a reacted mixture comprising the amide derivative. The ruthenium catalyst complex is represented by the following structural formula: RuX2(L)n, wherein X is an anionic ligand, L is a bifunctional phosphine ligand, and n is 3 or 4.
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(2013/04/24)