- Microwave-assisted efficient one-pot synthesis of nitriles from aldehydes in the presence of P2O5/SiO2 in solvent-free media
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A rapid and efficient procedure is developed for a one-pot synthesis of nitrites by condensation of aldehydes with hydroxylamine hydrochloride in the presence of P2O5/SiO2 in solvent-free media under microwave irradiation. Copyright Taylor & Francis Inc.
- Eshghi, Hossein,Gordi, Zinat
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- Studies of the chemical selectivity of hapten, reactivity, and skin sensitization potency. 1. Synthesis and studies on the reactivity toward model nucleophiles of the 13c-labeled skin sensitizers hex-1-ene- and hexane-1,3-sultones
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The potent skin sensitizers hex-1-ene- and hexane-1,3-sultone have been synthesized isotopically labeled with 13C at reactive sites. The reactivity of 2-[13C]- and 3-[13C]hex-1-ene-1,3-sultones and of 3-[13C]hexane-1,3-sultone toward a series of model nucleophiles for protein amino acid residues, i.e., butylamine, diethylamine, imidazole, propanethiol, and phenol, was followed by 13C NMR spectroscopy. The reactivity in water of hex-1-ene-1,3-sultone toward model nucleophiles follows the hard and soft acid and base theory with the hard nucleophiles (primary and secondary amine and phenate) mainly reacting at position 3 by SN substitution, and the soft nucleophiles (thiolate and imidazole) mainly reacting at position 2 by a Michael addition reaction. Hexane-1,3-sultone reacts with model nucleophiles at position 3 by SN substitution. Both saturated and unsaturated sultones are sensitive to hydrolysis when reacted in water.
- Meschkat, Emmanuel,Barratt, Martin D.,Lepoittevin, Jean-Pierre
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- Reaction of interstitial cyanide ions in a hydrotalcite-like material with organic chlorides
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A hydrotalcite-like material, Mg6Al2(OH)16Cl2-xCN x·4H2O (x= 1.53-1.94), was prepared and tested as a reagent for the nucleophilic substitution for chlorine atom of C6H5CH2Cl, C4H9Cl, and C3H7Cl by the CN ions in the interlayer of the material. The corresponding organic cyanides were obtained at 353 K in a non-polar solvent, toluene.
- Suzuki, Eiichi,Inoue, Atsushi,Ono, Yoshio
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- A Beckmann-Type Dehydration of n-Butyraldoxime Catalyzed by Cytochrome P-450
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n-Butyraldoxime undergoes a unique NADPH-dependent, Beckmann-type dehydration catalyzed by rat liver microsomes to give n-butyronitrile.
- DeMaster, Eugene G.,Shirota, Frances N.,Nagasawa, Herbert T.
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- Rhodium-Catalysed Asymmetric Hydroformylation of Unsaturated Nitriles
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Asymmetric hydroformylation of crotononitrile (1) and ally cyanide (2) was probed with the view to develop a synthesis for (R)-4-amino-2-methyl-butan-1-ol. Hydroformylation of 1 under a variety of conditions mainly led to hydrogenated product. Hydroformylation of 2 with Rh/tris(2,4-di-tert-butylphenyl) phosphite gave good selectivity to the formylated nitrile with an n/iso of 77:23. Asymmetric hydroformylation of 2 could be accomplished in 66% ee using Rh/(R,S)-BINAPHOS.
- Lambers-Verstappen, Marielle M.H.,De Vries, Johannes G.
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- The Question of Tautomerism of Alkylnitrile and Isonitrile Cations
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The isomeric pairs+. and +. and +. and +. have been established as stable, noninterconverting structures.The conclusion derives from studies of collision induced decomposition spectra.The same conclusion pertains for the ions +. and +., and for +., +. and HNCCHCHCNH>+..The energy barrier of a -hydrogen shift, a possible isomerization mechanism, is determined to be at least 163kJ mol-1 for the +. and +. pair, and the barrier may be as high as 318kJ*mol-1.The C3H5N and C4H4N2 radical cations decompose before they can be activated with 318 kJ mol-1 of internal energy.
- Chess, Edward K.,Lapp, R. L.,Gross, Michael L.
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- Purification and characterization of aldoxime dehydratase of the head blight fungus, Fusarium graminearum
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Fungal aldoxime dehydratase (Oxd) of Fusarium graminearum MAFF305135 was purified and characterized for the first time from its overexpressing Escherichia coli transformant. The enzyme showed about 20% identity with known Oxds, and had similar enzymatic properties with nitrilase-linked Oxd from the Bacillus strain. It belongs to a group of phenylacetaldoxime dehydratases (EC 4.99.1.7), based on its substrate specificity and kinetic analysis.
- Kato, Yasuo,Asano, Yasuhisa
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- Study on alumina-supported cobalt-nickel oxide catalyst for synthesis of acetonitrile from ethanol
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A new alumina-supported cobalt-nickel oxide catalyst for the synthesis of acetonitrile from ethanol and ammonia was prepared by coprecipitation-kneading method. The parameters influencing the reaction were studied thoroughly and an optimized process, which is running the reaction at 380 °C under atmospheric pressure while keeping the ammonia/alcohol molar ratio of 5 and GHSV of 1,163 h-1, was obtained. Under the optimized conditions the catalyst reached its best performance when being on stream for 40 h, at which the yield of acetonitrile was 92.6%. Then the selectivity to acetonitrile decreased gradually but the yield of acetonitrile always remained higher than 81% within 720 h. The samples of the fresh and used catalyst were characterized by XRD, XPS, TEM, EDX and N2 adsorption-desorption analysis. The results revealed that carbon deposition and formation of metal carbides from the active species in the catalytic runs led to the deterioration of the catalyst. Graphical Abstract: A new Co-Ni/γ-Al2O3 catalyst for the amination of ethanol to acetonitrile was studied in a continuous fixed-bed reactor and the reaction parameters were optimized. The mechanisms for the formation of acetonitrile and butyronitrile were discussed. The reasons leading to the deterioration of the catalyst were investigated through the characterization of the fresh, used and regenerated samples of the catalyst by means of XRD, XPS, TEM and N2 adsorption-desorption techniques.
- Feng, Cheng,Zhang, Yuecheng,Zhang, Yining,Wen, Yanlong,Zhao, Jiquan
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- Thermal Desorption and Infrared Studies of Primary Aliphatic Amines adsorbed on Haematite (α-Fe2O3)
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The adsorption of n-octadecylamine on α-Fe2O3 at the solid/liquid interface, and of n-butylamine at the solid/liquid and solid/vapour interfaces has been studied by infrared spectroscopy.To obtain further information about the nature of desorbing products, temperature-programmed desorption experiments were made with n-butylamine-α-Fe2O3 adsorbates.No difference could be detected by i.r. spectroscopy between the nature of adsorbates formed under the various mentioned conditions.Adsorption of n-octadecylamine and n-butylamine on α-Fe2O3 mainly involves coordinative interactions between amine and Lewis-acidic surface sites (Fe(3+) cations).Furthermore, hydrogen bonds are formed between surface hydroxy groups and adsorbed amine molecules. n-Butylamine adsorbed on α-Fe2O3 gave four different desorption peaks (I-IV) which are formed by n-butylamine (I:423 K), butyronitrile (II:530 K), CO2 (III:630K) and H2O (IV:713 K).Desorption of CO2 and H2O is caused by the oxidation of amine molecules strongly adsorbed on two different types of coordination sites.
- Marx, Ute,Sokoll, Rolf,Hobert, Hartmut
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- Linear-Organic-Polymer-Supported Iridium Complex as a Recyclable Auto-Tandem Catalyst for the Synthesis of Quinazolinones via Selective Hydration/Acceptorless Dehydrogenative Coupling from o-Aminobenzonitriles
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A linear-organic-polymer-supported iridium complex Cp*Ir@P4VP, which is designed and synthesized by the coordinative immobilization of [Cp*IrCl2]2 on poly(4-vinylpyridine), was proven to be an efficient heterogeneous autotandem catalyst for synthesizing quinazolinones via selective hydration/acceptorless dehydrogenative coupling from o-aminobenzonitriles. Furthermore, the synthesized catalyst was recycled five times without an obvious decrease in the catalytic activity.
- Hao, Shushu,Yang, Jiazhi,Liu, Peng,Xu, Jing,Yang, Chenchen,Li, Feng
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supporting information
p. 2553 - 2558
(2021/04/13)
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- Ambient Hydrogenation and Deuteration of Alkenes Using a Nanostructured Ni-Core–Shell Catalyst
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A general protocol for the selective hydrogenation and deuteration of a variety of alkenes is presented. Key to success for these reactions is the use of a specific nickel-graphitic shell-based core–shell-structured catalyst, which is conveniently prepared by impregnation and subsequent calcination of nickel nitrate on carbon at 450 °C under argon. Applying this nanostructured catalyst, both terminal and internal alkenes, which are of industrial and commercial importance, were selectively hydrogenated and deuterated at ambient conditions (room temperature, using 1 bar hydrogen or 1 bar deuterium), giving access to the corresponding alkanes and deuterium-labeled alkanes in good to excellent yields. The synthetic utility and practicability of this Ni-based hydrogenation protocol is demonstrated by gram-scale reactions as well as efficient catalyst recycling experiments.
- Beller, Matthias,Feng, Lu,Gao, Jie,Jackstell, Ralf,Jagadeesh, Rajenahally V.,Liu, Yuefeng,Ma, Rui
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supporting information
p. 18591 - 18598
(2021/06/28)
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- Facile dehydration of primary amides to nitriles catalyzed by lead salts: The anionic ligand matters
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The synthesis of nitrile under mild conditions was achieved via dehydration of primary amide using lead salts as catalyst. The reaction processes were intensified by not only adding surfactant but also continuously removing the only by-product, water from the system. Both aliphatic and aromatic nitriles can be prepared in this manner with moderate to excellent yields. The reaction mechanisms were obtained with high-level quantum chemical calculations, and the crucial role the anionic ligand plays in the transformations were revealed.
- Ruan, Shixiang,Ruan, Jiancheng,Chen, Xinzhi,Zhou, Shaodong
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- Enantioselective Radical Carbocyanation of 1,3-Dienes via Photocatalytic Generation of Allylcopper Complexes
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1,3-Dienes are readily available feedstocks that are widely used in the laboratory and industry. However, the potential of converting 1,3-dienes into value-Added products, especially chiral products, has not yet been fully exploited. By synergetic photoredox/copper catalysis, we achieve the first visible-light-induced, enantioselective carbocyanation of 1,3-dienes by using carboxylic acid derivatives and trimethylsilyl cyanide. Under mild and neutral conditions, a diverse range of chiral allyl cyanides are produced in generally good efficiency and with high enantioselectivity from bench-stable and user-safe chemicals. Moreover, preliminary results also confirm that this success can be expanded to 1,3-enynes and the four-component carbonylative carbocyanation of 1,3-dienes and 1,3-enynes.
- Lu, Fu-Dong,Lu, Liang-Qiu,He, Gui-Feng,Bai, Jun-Chuan,Xiao, Wen-Jing
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supporting information
p. 4168 - 4173
(2021/04/06)
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- Method for continuous preparation of nitriles in a pipelined reactor (by machine translation)
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The method comprises the following steps that a tin catalyst is coated on the inner wall of the pipeline reactor; and the method comprises the following steps: coating a tin catalyst on the inner wall of the pipeline reactor. The amide solution and the catalytic auxiliary agent are mixed and then sent to a pipeline reactor, and the amide is dehydrated to generate nitrile at the reaction pressure of 0.1 - 2.0 mpa and 100 - 200 °C reaction temperature. The resulting reaction product was separated to give the crude product of the nitrile to which the amide corresponded. In the pipeline reactor, the corresponding nitrile is continuously prepared under the action of the tin catalyst, a dehydrating agent is not needed, byproducts only are water, and three wastes are reduced. (by machine translation)
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Paragraph 0036-0047; 0056; 0058
(2020/12/14)
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- Method for continuous preparation of nitriles by amides (by machine translation)
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The method comprises the following steps: preparing a lead salt supported by a molecular sieve by a lead salt and a molecular sieve through an impregnation method; and filling a molecular sieve-loaded lead catalyst into a fixed bed reactor. The amide or amide solution is sent into a fixed bed reactor from the top of the fixed bed to be subjected to catalytic dehydration, and the obtained reaction product is led out from the bottom of the fixed bed. The reaction product is separated to obtain the crude product of the nitrile corresponding to the amide. A fixed bed continuous production process is adopted, the reaction process is simple, the production efficiency is high, the product post-treatment is simple, and industrial production is easy to realize. (by machine translation)
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Paragraph 0033-0054; 0061-0066
(2020/12/15)
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- Rhodium Porphyrin Catalyzed Regioselective Transfer Hydrogenolysis of C-C σ-Bonds in Cyclopropanes with iPrOH
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A new rhodium porphyrin catalyzed regioselective transfer hydrogenolysis of both activated and unactivated cyclopropanes employing iPrOH as the hydrogen source was discovered. The reaction mechanism for the C-C σ-bond activation of cyclopropanes was identified through an initial radical substitution with rhodium(II) metalloporphyrin radical to give a rhodium porphyrin alkyl, followed by hydrogenolysis with iPrOH to give the corresponding acyclic alkanes and regenerate rhodium(II) metalloporphyrin radical.
- Chen, Chen,Feng, Shiyu,Chan, Kin Shing
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p. 2582 - 2589
(2019/07/02)
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- A method of synthesizing fatty nitrile by the aliphatic aldehyde
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The invention relates to a method of synthesizing fatty nitrile by the aliphatic aldehyde. The method comprises the following steps: the aliphatic aldehyde, ionic liquid regenerating and ionic liquid in the reactor, to join the two toluene, stirring, of the reflux condensation, in the normal pressure, 90 - 120 °C reaction under 0.5 - 2 h, to obtain the product fatty nitrile; wherein said ionic liquid is 1 - sulfobutyl pyridine bisulphate ionic liquid; ion liquid hydroxylamine salt is 1 - sulfobutyl pyridine bisulphate ion liquid hydroxylamine salt. The invention in one reactor to achieve the fat [...] and fat aldoxime dehydration integrated two-step reaction, the process is simple, easy to operate; to ionic liquid as catalyst and a co-solvent, without the addition of metal salt catalyst and corrosive solvent, environment-friendly.
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Paragraph 0027; 0028; 0041; 0042
(2019/05/28)
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- Green synthesis of benzonitrile using ionic liquid with multiple roles as the recycling agent
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Preparation of benzonitrile from benzaldehyde and hydroxylamine hydrochloride is one of the most advantageous approaches. Nevertheless, it suffers from various constraints such as longer reaction time, corrosion and recovery of hydrochloric acid, the use of metal salt catalysts and their separation. For these reasons, a novel green benzonitrile synthetic route was proposed with ionic liquid as the recycling agent in this study. The results indicated that hydroxylamine 1-sulfobutyl pyridine hydrosulfate salt ((NH2OH)2·[HSO3-b-Py]·HSO4) was an expert alternative to hydroxylamine hydrochloride. Meanwhile, the ionic liquid [HSO3-b-Py]·HSO4 exhibited the multiple roles of co-solvent, catalysis and phase separation, thus the use of metal salt catalyst was eliminated, and no additional catalyst was needed. Hence, the separation process was greatly simplified. When the molar ratio of benzaldehyde to (NH2OH)2·[HSO3-b-Py]·HSO4 was 1:1.5, the volume ratio of paraxylene to [HSO3-b-Py]·HSO4 was 2:1, the benzaldehyde conversion and benzonitrile yield were both 100% at 120 °C in 2 h. Even better, the ionic liquid could be recovered easily by phase separation, and recycled directly after reaction. Additionally, this novel route is applicable to the green synthesis of a variety of aromatic, heteroaromatic and aliphatic nitriles with excellent yields.
- Li, Zhihui,Wang, Tingting,Qi, Xudong,Yang, Qiusheng,Gao, Liya,Zhang, Dongsheng,Zhao, Xinqiang,Wang, Yanji
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p. 17631 - 17638
(2019/06/24)
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- Synthesis of: N -unsubstituted cycloalkylimines containing a 4 to 8-membered ring
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Primary cycloalkylimines with a 4 to 8-membered ring were synthesized by dehydrocyanation of the corresponding α-aminonitriles on solid potassium hydroxide via a vacuum gas-solid reaction. Imine-enamine tautomerism has been demonstrated at room temperature for the most kinetically stable derivatives.
- Guillemin, Jean-Claude,Nasraoui, Wafa,Gazzeh, Houda
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supporting information
p. 5647 - 5650
(2019/05/21)
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- Selective Transformations of Triglycerides into Fatty Amines, Amides, and Nitriles by using Heterogeneous Catalysis
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The use of triglycerides as an important class of biomass is an effective strategy to realize a more sustainable society. Herein, three heterogeneous catalytic methods are reported for the selective one-pot transformation of triglycerides into value-added chemicals: i) the reductive amination of triglycerides into fatty amines with aqueous NH3 under H2 promoted by ZrO2-supported Pt clusters; ii) the amidation of triglycerides under gaseous NH3 catalyzed by high-silica H-beta (Hβ) zeolite at 180 °C; iii) the Hβ-promoted synthesis of nitriles from triglycerides and gaseous NH3 at 220 °C. These methods are widely applicable to the transformation of various triglycerides (C4–C18 skeletons) into the corresponding amines, amides, and nitriles.
- Jamil, Md. A. R.,Siddiki, S. M. A. Hakim,Touchy, Abeda Sultana,Rashed, Md. Nurnobi,Poly, Sharmin Sultana,Jing, Yuan,Ting, Kah Wei,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-ichi
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p. 3115 - 3125
(2019/04/26)
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- Identification of an Active NiCu Catalyst for Nitrile Synthesis from Alcohol
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Development of heterogeneous catalysts for alcohol transformation into nitriles under oxidant-free conditions is a challenge. Considering the C-H activation on α-carbon of primary alcohols is the rate-determining step, decreasing the activation energy of C-H activation is critical in order to enhance the catalytic activity. Several NiM/Al2O3 bimetallic catalysts were synthesized and scrutinized in catalytic transformation of 1-butanol to butyronitrile. Ni-Cu was identified as a suitable combination with the optimized Ni0.5Cu0.5/Al2O3 catalyst exhibiting 10 times higher turnover frequency than Ni/Al2O3 catalyst. X-ray absorption spectroscopy (XAS) and high angle annular dark field scanning transmission electron microscopy (HAADF-STEM) revealed that the NiCu particles in the catalyst exist in the form of homogeneous alloys with an average size of 8.3 nm, providing an experimental foundation to build up a catalyst model for further density functional theory (DFT) calculations. Calculations were done over a series of NiM catalysts, and the experimentally observed activity trend could be rationalized by the Br?nsted-Evans-Polanyi (BEP) principle, i.e., catalysts that afford reduced reaction energy also feature lower activation barriers. The calculated activation energy (Ea) for C-H activation with coadsorbed NH3 dropped from 63.4 kJ/mol on pure Ni catalyst to 49.9 kJ/mol on the most active NiCu-2 site in NiCu bimetallic catalyst, in good agreement with the experimentally measured activation energy values. The Ni0.5Cu0.5/Al2O3 catalyst was further employed to convert 11 primary alcohols into nitriles with high to near-quantitative yields, at a Ni loading 10 times less than that of the conventional Ni/Al2O3 catalyst.
- Wang, Yunzhu,Furukawa, Shinya,Yan, Ning
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p. 6681 - 6691
(2019/07/12)
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- Oxidant free conversion of alcohols to nitriles over Ni-based catalysts
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Organic nitriles are significant and versatile industrial feedstocks, but their conventional synthetic protocols require hazardous starting materials and/or harsh reaction conditions posing environmental and health risks. Herein, we established a Ni-based catalytic system to convert primary alcohols to nitriles with ammonia gas as the sole nitrogen source under oxidant-free conditions at merely 190-230 °C. Based on isotope labelling experiments, in situ DRIFTS and control experiments, the reaction pathway was identified to follow a dehydrogenation-imination-dehydrogenation sequence, with α-carbon C-H bond breakage as the rate determining step. Ni is superior to all noble metal catalysts tested, due to its excellent dehydrogenation ability that is not inhibited by NH3. The support plays an auxiliary role, promoting the reaction between aldehyde and ammonia to form imine as a critical intermediate. Ni/Al2O3 catalyst prepared via a deposition-precipitation method, featuring both excellent dispersion of metallic Ni and suitable acid sites, enabled alcohol transformation into nitrile under unprecedented low temperature. Various alcohols were converted into their corresponding nitriles in high conversions and yields (both up to 99%), while the catalyst kept 90% of its original activity after 48 hours in the stability test, highlighting the wide applicability and the robustness of the catalytic system.
- Wang, Yunzhu,Furukawa, Shinya,Zhang, Zhang,Torrente-Murciano, Laura,Khan, Saif A.,Yan, Ning
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- Double Dehydrogenation of Primary Amines to Nitriles by a Ruthenium Complex Featuring Pyrazole Functionality
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A ruthenium(II) complex bearing a naphthyridine-functionalized pyrazole ligand catalyzes oxidant-free and acceptorless selective double dehydrogenation of primary amines to nitriles at moderate temperature. The role of the proton-responsive entity on the ligand scaffold is demonstrated by control experiments, including the use of a N-methylated pyrazole analogue. DFT calculations reveal intricate hydride and proton transfers to achieve the overall elimination of 2 equiv of H2.
- Dutta, Indranil,Yadav, Sudhir,Sarbajna, Abir,De, Subhabrata,H?lscher, Markus,Leitner, Walter,Bera, Jitendra K.
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supporting information
p. 8662 - 8666
(2018/07/09)
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- A method for the preparation of nitrile compounds amine catalysis oxidation method
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A method for preparing nitrile compounds by catalytic oxidation of amine can catalyze amine to oxidize and synthesize the nitrile compounds high efficiently and high selectively under the condition of normal pressure and normal temperature by using peroxide as an oxidizing agent. The method for preparing nitrile compounds by catalytic oxidation of amine has mild operation condition. The conversion rate of amine can be reached to 92%, and the selectivity of the nitrile compounds can be reached to 95%.
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Paragraph 0036; 0037
(2017/07/04)
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- Nitrilation of carboxylic acids with acetonitrile catalyzed by molybdenum and vanadium complexes
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Various carbonitriles were synthesized by reaction of the corresponding carboxylic acids with acetonitrile in carbon tetrachloride in the presence of VO(acac)2and Mo(CO)6in 6 h at 150–170°C.
- Khusnutdinov,Shchadneva,Bayguzina,Mayakova, Yu. Yu.
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p. 1282 - 1286
(2016/10/26)
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- Quinazolinones from o-Aminobenzonitriles by One-Pot Sequential Selective Hydration/Condensation/Acceptorless Dehydrogenation Catalyzed by an Iridium Complex
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A new strategy for the direct synthesis of quinazolinones from o-aminobenzonitriles was proposed and accomplished. In the presence of [Cp?IrCl2]2 (Cp?=pentamethylcyclopentadienyl), a variety of desirable products was obtained easily through the one-pot sequential selective hydration/condensation/acceptorless dehydrogenation. This protocol is highly attractive because it uses readily available starting materials, has a high atom efficiency, good to excellent yields, and minimal consumption of chemicals and energy. Notably, this research exhibited new potential for the development of transition-metal-catalyzed one-pot sequential reactions that involve acceptorless dehydrogenation.
- Zhao, Wei,Liu, Pengcheng,Li, Feng
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p. 1523 - 1530
(2016/05/02)
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- Selective hydrogenation of nitriles to primary amines catalyzed by a novel iron complex
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Hydrogenation of nitriles to primary amines constitutes an atom-efficient and environmentally benign synthetic reaction. Herein we present a novel complex based on earth-abundant iron, and its application in the catalytic homogeneous hydrogenation of (hetero)aromatic, benzylic, and aliphatic nitriles to selectively form primary amines.
- Chakraborty, Subrata,Leitus, Gregory,Milstein, David
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supporting information
p. 1812 - 1815
(2016/02/05)
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- Nanopalladium-catalyzed conjugate reduction of Michael acceptors-application in flow
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A continuous-flow approach towards the selective nanopalladium-catalyzed hydrogenation of the olefinic bond in various Michael acceptors, which could lead to a greener and more sustainable process, has been developed. The nanopalladium is supported on aminofunctionalized mesocellular foam. Both aromatic and aliphatic substrates, covering a variation of functional groups such as acids, aldehydes, esters, ketones, and nitriles were selectively hydrogenated in high to excellent yields using two different flow-devices (H-Cube and Vapourtec). The catalyst was able to hydrogenate cinnamaldehyde continuously for 24 h (in total hydrogenating 19 g cinnanmaldehyde using 70 mg of catalyst in the H-cube) without showing any significant decrease in activity or selectivity. Furthermore, the metal leaching of the catalyst was found to be very low (ppb amounts) in the two flow devices.
- Nagendiran, Anuja,S?rensen, Henrik,Johansson, Magnus J.,Tai, Cheuk-Wai,B?ckvall, Jan-E.
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supporting information
p. 2632 - 2637
(2016/05/24)
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- Mechanistic insights into the oxidative dehydrogenation of amines to nitriles in continuous flow
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The oxidative dehydrogenation of various aliphatic amines to their corresponding nitrile compounds using RuO2/Al2O3 catalysts in air was successfully applied to a continuous flow reaction. Conversions of amines (up to >99%) and yields of nitriles (up to 77%) varied depending on reaction conditions and the amine utilised. The presence of water was found to be important for the activity and stability of the RuO2/Al2O3 catalyst. The Hammett relationship and in situ infrared spectroscopy were applied to divulge details about the catalytic mechanism of the oxidative dehydrogenation of amines over RuO2/Al2O3 catalysts.
- Corker, Emily C.,Ruiz-Martínez, Javier,Riisager, Anders,Fehrmann, Rasmus
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p. 5008 - 5015
(2015/11/03)
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- Highly efficient aerobic oxidation of various amines using Pd3Pb intermetallic compounds as catalysts
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Intermetallic Pd3Pb supported on Al2O3 can act as a highly efficient heterogeneous catalyst for the oxidation of various amines including primary, secondary, aromatic, aliphatic, and cyclic amines. The Royal Society of Chemistry 2014.
- Furukawa, Shinya,Suga, Akifusa,Komatsu, Takayuki
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p. 3277 - 3280
(2014/03/21)
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- Chitosan supported ionic liquid: A recyclable wet and dry catalyst for the direct conversion of aldehydes into nitriles and amides under mild conditions
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A green and highly efficient chitosan supported magnetic ionic liquid (CSMIL) was synthesized with chitosan (the most abundant biopolymer in nature and a cheap industrial waste product), methyl imidazole and anhydrous/hydrous FeCl3. The heterogeneous catalyst thus obtained was used for the direct conversion of aldehydes to the corresponding nitriles in the presence of NH2OH·HCl/dry-CSMIL/MeSO2Cl and amides with NH 2OH·HCl/wet-CSMIL/MeSO2Cl. A highlight of our approach is the easy separation of the catalyst from the reaction medium and thus the recyclability of the catalyst. This simple method can be applied to obtain a wide range of aromatic, heterocyclic, and aliphatic nitriles and amides.
- Khalafi-Nezhad, Ali,Mohammadi, Somayeh
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p. 13782 - 13787
(2014/04/17)
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- One-step synthesis of nitriles by the dehydrogenation-amination of fatty primary alcohols over Cu/m-ZrO2
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An effective method for one-step synthesis of nitriles employing C 2-C8 fatty primary alcohols and ammonia over 5%Cu/m-ZrO2 has been found. The conversion of alcohols and selectivity of nitriles obtained are > 96 and > 87 wt.%, respectively, and are obviously influenced by the C2-substitution rather than the chain length of fatty primary alcohols. Cu/m-ZrO2 was characterized by XRD, H 2-TPR, CO2-TPD and NH3-TPD. It is revealed that a substantial amount of Cu species over m-ZrO2 is in highly dispersed CuO. A plausible mechanism is proposed and supported by different experiments, and aldehyde generation is an important step in the reaction mechanism.
- Hu, Yunfeng,Jin, Shuhan,Zhang, Zhichao,Zhang, Likun,Deng, Jun,Zhang, Hongsheng
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- A procedure for Appel halogenations and dehydrations using a polystyrene supported phosphine oxide
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The conversion of a commercially available polystyrene supported phosphine oxide into synthetically useful polymeric halophosphonium salts using oxalyl chloride/bromide takes place at room temperature in 5 min and generates only CO and CO2 as by-products. The polymeric halophosphonium salts so obtained are useful reagents for Appel halogenations and other dehydrative coupling reactions. This gives rise to a simple three-step synthesis cycle for Appel and related reactions using a commercially available polymeric phosphine oxide with very simple purification and no phosphorus waste.
- Tang, Xiaoping,An, Jie,Denton, Ross M.
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p. 799 - 802
(2014/02/14)
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- Oxidative Degradation of Amino Acids and Aminophosphonic Acids by 2,2′-Bipyridine Complexes of Copper(II)
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Copper(II)-amino acid (AA) complexes that contain 2,2′-bipyridine (bpy) as supporting ligand were investigated. X-ray structural analysis of three new bpy-based complexes revealed a bidentate coordination of the AAs on the copper(II) centers similar to that proposed for the substrate on the iron(II) center of the 1-aminocyclopropane-1-carboxylic acid oxidase (ACCO). Similar complexes with two aminophosphonic acids (APAs), 1-aminocyclopropane-1-phosphonic acid (ACP) and (1-amino-1-methyl)ethylphosphonic acid (AMEP), were also investigated, and the latter complex was structurally characterized. This structure reveals the bidentate coordination of α-aminophosphonate on the copper(II) ion. The oxidation of the bound amino acids (AAs) and aminophosphonates (APAs), which model the reaction catalyzed by ACCO, was investigated. The complexes react with H2O2 and give oxidation products that were identified by gas chromatography. Reduction of CuII to CuI was detected by UV/Vis spectroscopy upon reaction with H2O2 or ascorbate. This reduction is proposed to be the initial step for the peroxide/copper activation prior to the oxidation of the AA and APA ligands by means of a radical mechanism.
- Pap, József S.,El Bakkali-Tahéri, Nadia,Fadel, Antoine,Góger, Szabina,Bogáth, Dóra,Molnár, Milán,Giorgi, Michel,Speier, Gábor,Simaan, A. Jalila,Kaizer, József
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p. 2829 - 2838
(2015/04/27)
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- Thermal decomposition of diethylketone cyclic triperoxide in polar solvents
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The thermolysis of diethylketone cyclic triperoxide (3,3,6,6,9,9-hexaethyl- 1,2,4,5,7,8-hexaoxacyclononane, DEKTP) was studied in different polar solvents (ethanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-2-propanol, and acetonitrile). The rate constant values (kd) are higher for reactions performed in secondary alcohols probably because of the possibility to form a cyclic adduct with the participation of the hydrogen atom bonded to the secondary carbon. The kinetic parameters were correlated with the physicochemical properties of the selected solvents. The products of the DEKTP thermal decomposition in different polar solvents support a radical-based decomposition mechanism. CSIRO 2014.
- Barreto, Gaston P.,Alvarez, Elida E.,Eyler, Gladys N.,Canizo, Adriana I.,Allegretti, Patricia E.
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p. 881 - 886
(2014/07/07)
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- Oxidative degradation of amino acids and aminophosphonic acids by 2,2′-bipyridine complexes of copper(II)
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Copper(II)-amino acid (AA) complexes that contain 2,2′-bipyridine (bpy) as supporting ligand were investigated. X-ray structural analysis of three new bpy-based complexes revealed a bidentate coordination of the AAs on the copper(II) centers similar to that proposed for the substrate on the iron(II) center of the 1-aminocyclopropane-1-carboxylic acid oxidase (ACCO). Similar complexes with two aminophosphonic acids (APAs), 1-aminocyclopropane-1- phosphonic acid (ACP) and (1-amino-1-methyl)ethylphosphonic acid (AMEP), were also investigated, and the latter complex was structurally characterized. This structure reveals the bidentate coordination of α-aminophosphonate on the copper(II) ion. The oxidation of the bound amino acids (AAs) and aminophosphonates (APAs), which model the reaction catalyzed by ACCO, was investigated. The complexes react with H2O2 and give oxidation products that were identified by gas chromatography. Reduction of CuII to CuI was detected by UV/Vis spectroscopy upon reaction with H2O2 or ascorbate. This reduction is proposed to be the initial step for the peroxide/copper activation prior to the oxidation of the AA and APA ligands by means of a radical mechanism. The oxidation of bound amino acids or aminophosphonic acids by copper(II) complexes, which models the reaction catalyzed by the 1-aminocyclopropane carboxylic acid oxidase, was investigated in the presence of hydrogen peroxide. A reaction mechanism that involves a CuI intermediate is discussed. Copyright
- Pap, J?zsef S.,El Bakkali-Tahéri, Nadia,Fadel, Antoine,G?ger, Szabina,Bogáth, D?ra,Molnár, Milán,Giorgi, Michel,Speier, Gábor,Simaan, A. Jalila,Kaizer, J?zsef
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p. 2829 - 2838
(2014/06/24)
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- Copper catalyzed oxidation of amino acids
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Copper(II) chloride and novel bis(1-amino(cyclo)alkane-1-carboxylato- κ2N,O)copper(II) complexes as catalysts were studied in relation with enzymatic oxidation of amino acids. The oxidation of aminophosphonate derivative: (1-amino-1-methyl)ethylphosphonic acid was also investigated. Two bis(1-aminocycloalkane-1-carboxylato-κ2N,O) copper(II) complexes were structurally characterized. Surprisingly, while the 1-aminocyclobutane-1-carboxylate complex has square planar (SP-4) copper(II) center with trans-orientated ligands, the 1-aminocyclohexane-1-carboxylate complex has μ-carboxylato dimeric structure with square pyramidal (SPY-5) sites, one with cis- and one with trans-orientated ligands. Redox behavior of the bis(1-amino(cyclo)alkane-1-carboxylato-κ2N,O)copper(II) complexes was also investigated. Catalytic oxidations were carried out in alkaline DMF-water mixtures using H2O2 as oxidant and the complexes as catalysts. The observed potentials for the irreversible current peaks associated with the Cu(II) to Cu(I) reduction and the rates of the amino acid oxidations show inverse trend. This suggests that the Cu(II)/Cu(I) redox cycling due to the presence of H2O2 plays important role in the peroxide/copper activation that in turn provides the observed products.
- Góger, Szabina,Pap, József S.,Bogáth, Dóra,Simaan, A. Jalila,Speier, Gábor,Giorgi, Michel,Kaizer, József
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- Palladium on charcoal as a catalyst for stoichiometric chemo- and stereoselective hydrosilylations and hydrogenations with triethylsilane
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Stoichiometric quantities of triethylsilane in the presence of activated Pd/C as the catalyst can be used to effect chemo-, regio-, and stereoselective hydrosilylation and transfer hydrogenation reactions. α,β-Unsaturated aldehydes and ketones are selectively hydrosilylated to give the corresponding enol silanes or transfer hydrogenated to give the saturated carbonyl compounds in the presence of other reducible functional groups.
- Tuokko, Sakari,Pihko, Petri M.
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p. 1740 - 1751
(2015/02/19)
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- One-step synthesis of nitriles by the dehydrogenation-amination of fatty primary alcohols over Cu/m-ZrO2
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An effective method for one-step synthesis of nitriles employing C2-C8 fatty primary alcohols and ammonia over 5%Cu/m-ZrO2 has been found. The conversion of alcohols and selectivity of nitriles obtained are > 96 and > 87 wt.%, respectively, and are obviously influenced by the C2-substitution rather than the chain length of fatty primary alcohols. Cu/m-ZrO2 was characterized by XRD, H2-TPR, CO2-TPD and NH3-TPD. It is revealed that a substantial amount of Cu species over m-ZrO2 is in highly dispersed CuO. A plausible mechanism is proposed and supported by different experiments, and aldehyde generation is an important step in the reaction mechanism.
- Hu, Yunfeng,Jin, Shuhan,Zhang, Zhichao,Zhang, Likun,Deng, Jun,Zhang, Hongsheng
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- Direct synthesis of nitriles from alcohols or aldehydes using H 5IO 6/KI in aqueous ammonia
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The oxidative conversion of alcohols or aldehydes to the corresponding nitriles in moderate to good yields was easily achieved by treatment of H 5IO6 and KI in aqueous NH3. This simple and one-pot system provides easy workup and separation of the product. Copyright
- Ghorbani-Choghamarani, Arash,Sardari, Sara,Zolfigol, Mohammad Ali,Hajjami, Maryam
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p. 52 - 58,7
(2020/08/24)
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- An efficient, rapid and facile procedure for conversion of aldoximes to nitriles using triphenylphosphine and N-halo sulfonamides
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N,N,N′,N′-Tetrabromobenzene-1,3-disulfonamide (TBBDA)/triphenylphosphine and N,N,N′,N′-tetrachlorobenzene-1,3- disulfonamide (TCBDA)/triphenylphosphine have been introduced as highly efficient systems for the versatile conversion of aldoxime derivatives into nitriles. The process reported here is operationally simple and reactions have been mildly performed in dichloromethane at room temperature.
- Ghorbani-Vaghei, Ramin,Shiri, Lotfi,Ghorbani-Choghamarani, Arash
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p. 1123 - 1126
(2014/01/06)
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- Conversion of aldoximes into nitriles and amides under mild conditions
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A series of Pd(en)X2 salts were used as catalysts for the conversion of aldoximes into nitriles and amides. Highlights of this protocol include the use of inexpensive polar solvents, including water, and moderate reaction temperatures. A high degree of selectivity in the reaction outcome was observed when using aliphatic vs. aromatic/conjugated aldoximes. The Royal Society of Chemistry 2013.
- Tambara, Koujiro,Pantos, G. Dan
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supporting information
p. 2466 - 2472
(2013/06/05)
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- Heterogeneous catalytic method for the conversion of aldoximes into nitriles using molecular sieve modified with Copper(II)
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A simple heterogeneous metal-catalyzed method was developed for the transformation of aldoximes into nitriles. Molecular sieve (4 A) modified with copper(II) proved to be an efficient catalyst for the conversion. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Kiss, Arpad,Hell, Zoltan
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supporting information
p. 1778 - 1786
(2013/05/22)
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- Novel ruthenium-terpyridyl complex for direct oxidation of amines to nitriles
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High catalytic activity and selectivity has been demonstrated for the oxidation of both aliphatic and aromatic amines to nitriles under benign conditions with dioxygen or air using the Ru2Cl4(az-tpy) 2 complex. The conversion was found to be strongly influenced by the alkyl chain length of the reactant with shorter chain amines found to have lower conversions than those with longer chains. Importantly, by using the ruthenium terpyridine complex functionalized with azulenyl moiety at the 4 position of central pyridine core provided a much higher reactivity catalyst compared with a series of ruthenium terpyridine-based ligand complexes reported. Mechanistic studies using deuterated benzylamine demonstrated the importance of RuOH in this reaction.
- Cristian, Liliana,Nica, Simona,Pavel, Octavian D.,Mihailciuc, Constantin,Almasan, Valer,Coman, Simona M.,Hardacre, Christopher,Parvulescu, Vasile I.
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p. 2646 - 2653
(2013/09/24)
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- Phosphonium salt-catalysed synthesis of nitriles from in situ activated oximes
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A metal-free catalytic method for the conversion of aromatic and aliphatic aldoximes to nitriles at room temperature using oxalyl chloride (1.2 equiv) in combination with 5 mol % of triphenylphosphine oxide is reported. Of the many potential pathways leading from oxime to nitrile a manifold involving chlorophosphonium salt-catalysed decomposition of oxime chlorooxalates formed in situ is shown to be operative.
- Denton, Ross M.,An, Jie,Lindovska, Petra,Lewis, William
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supporting information; experimental part
p. 2899 - 2905
(2012/05/05)
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- Cyclic aromatic analogues of the hendrickson reagent; NMR studies and electrophilic properties
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Two novel cyclic aromatic analogues of the Hendrickson POP reagent, 1,1,3,3-tetraphenyl-1,3-dihydro-2,1,3-benzoxadiphosphole-1,3-diium bis(trifluoromethanesulfinate) and bis(trifluoromethanesulfonate), have been readily prepared by the treatment of 1,2-bis(diphenylphosphino)benzene or 1,2-bis(diphenylphosphoryl)benzene, respectively, with trifluoromethanesulfonic anhydride in dichloromethane. 31P and 19F NMR studies indicated that while the latter complex is formed as the sole product, the former species was shown to be the predominant component in equilibrium with 1-(diphenylphosphino)-2-[diphenyl(trifluoromethylsulfonyloxy)phosphonio]benzene trifluoromethanesulfinate and 1,2-bis[diphenyl(trifluoromethylsulfonyloxy) phosphonio]benzene bis(trifluoromethanesulfinate). The dehydrating POP systems were exploited in the conversion of aldoximes into nitriles. The dehydration occurred rapidly at room temperature and produced high yields with a variety of alkyl- and arylaldoximes, tolerating a wide range of substrates and functional groups. Georg Thieme Verlag Stuttgart New York.
- Moussa, Ziad
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experimental part
p. 460 - 468
(2012/03/11)
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- 8-Bromocaffeine (8-BC): A new versatile reagent for conversion of aldoximes into nitriles
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A rapid and highly convenient synthesis of nitriles from the corresponding aldoximes using 8-bromocaffeine (8-BC) is described. In this protocol, aldoximes react with 8-BC in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and N,N-dimethylformamide (DMF) to furnish the corresponding nitriles under both microwave-assisted and/or conventional heating (reflux) conditions in short times and in good to excellent yields. This methodology is highly efficient for structurally diverse aldoximes including aliphatic, aromatic, and heteroaromatic oximes. Georg Thieme Verlag Stuttgart · New York.
- Soltani Rad, Mohammad Navid,Behrouz, Somayeh,Nekoei, Abdo-Reza
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experimental part
p. 1191 - 1198
(2012/06/04)
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- Lewis acid-catalyzed oxidation of benzylamines to benzamides
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A novel Lewis acid-catalyzed oxidation of benzylamines to the corresponding amides has been developed. Using 10 mol% of ZnBr2 or FeCl 3 as the catalyst and TBHP as the oxidant, amides were produced under mild conditions. The Royal Society of Chemistry 2012..
- Wu, Xiao-Feng,Bheeter, Charles Beromeo,Neumann, Helfried,Dixneuf, Pierre H.,Beller, Matthias
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supporting information
p. 12237 - 12239
(2013/01/16)
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- A mild and efficient rhenium-catalyzed transfer hydrogenation of terminal olefins using alcoholysis of amine-borane adducts as a reducing system
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[ReBr2(NO)(CH3CN)(PTA)2] (PTA = 1, 3, 5-triaza-7-phosphaadamantane) catalyzes the alcoholysis of ammonia-borane and amine-boranes and the catalytic transfer hydrogenations of various terminal olefins. Excellent yields were achieved at 70 °C in isopropanol using tBuOK as a co-catalyst affording TOF values up to 396 h-1.
- Dong, Hailin,Berke, Heinz
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experimental part
p. 1803 - 1808
(2011/06/19)
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- Ligand-free nickel-catalyzed conversion of aldoximes into nitriles
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Catalytic dehydration of aldoximes can be performed efficiently with NiCl2 in acetonitrile under neutral and mild conditions. Under these conditions, various functionalized aldoximes produce the corresponding nitriles in good to excellent yields. Georg Thieme Verlag Stuttgart. New York.
- Li, Yen-Ting,Liao, Bei-Sih,Chen, Hsin-Pei,Liu, Shiuh-Tzung
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experimental part
p. 2639 - 2643
(2011/10/04)
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- An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride (T3P)
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An efficient method for the Beckmann rearrangement of ketoximes to amides mediated by a catalytic amount (15 mol %) of propylphosphonic anhydride (T3P) is described. Aldoximes underwent second order Beckmann rearrangement to provide the corresponding nitriles in excellent yields on reacting with T3P (15 mol %) at room temperature. The main advantages of this environmentally friendly protocol include procedural simplicity, and particularly ease of isolation of the products.
- Augustine, John Kallikat,Kumar, Rajesha,Bombrun, Agnes,Mandal, Ashis Baran
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scheme or table
p. 1074 - 1077
(2011/03/22)
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- Efficient dehydration of aldoximes to nitriles catalyzed by a Lewis acid ionic liquid
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A Lewis acid ionic liquid, 1-[4-(chlorosulfonyl)butyl]-3-methylimidazolium chlorosulfate ([CBMIm]SO3Cl), with Lewis acid sites in both the anion and cation was synthesized. This was demonstrated to be an efficient catalyst for dehydration of aldoximes to nitriles. An unexpected self-induced phase separation of the reaction mixture was observed when the reaction was carried out in acetonitrile. This could be attributed to the hydrolysis of [CBMIm]SO3Cl to regenerate 1-(4-sulfobutyl)-3-methylimidazolium hydrogensulfate ([SBMIm]HSO4), which was the Bronsted precursor of [CBMIm]SO3Cl.
- Nakajima, Mizuki,Qiao, Kun,Kobayashi, Nobuhisa,Bao, Quanxi,Tomida, Daisuke,Yokoyama, Chiaki
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experimental part
p. 396 - 397
(2011/05/04)
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- Simple and highly efficient procedure for conversion of aldoximes to nitriles using N-(p-Toluenesulfonyl) imidazole
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A facile and efficient method for dehydration of aldoximes into nitriles using N-(p-toluenesulfonyl) imidazole (TsIm) is described. In this method, aldoximes were refluxed with TsIm in the presence of 1,8-diazabicyclo-[5.4.0] undec-7-ene (DBU) in dimethylformamide (DMF) to afford the corresponding nitriles in good yields. This methodology is highly efficient for various structurally diverse aldoximes including aromatic, heteroaromatic, and aliphatic oximes. A plausible mechanism for the conversion of aldoxime into nitriles using TsIm/DBU is explained. Copyright Taylor & Francis Group, LLC.
- Rad, Mohammad Navid Soltani,Khalafi-Nezhad, Ali,Behrouz, Somayeh,Amini, Zohreh,Behrouz, Marzieh
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experimental part
p. 2429 - 2440
(2010/09/05)
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- NMR Studies and electrophilic properties of triphenylphosphine-trifluoromethanesulfonic anhydride; a remarkable dehydrating reagent system for the conversion of aldoximes into nitriles
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NMR Studies on the reaction of triphenylphosphine with various amounts of triflic anhydride at 0 °C is described. The reagent structure resulting from mixing 1.3 equiv of Ph3P with Tf2O (1.0 mmol) has been established as an equilibrium mixture consisting mainly of triphenyl(trifluoromethylsulfonyloxy)phosphonium trifluoromethanesulfinate and the corresponding bis(triphenyl)oxodiphosphonium trifluoromethanesulfinate dimer. The electrophilic properties of the system have been exploited in the development of a mild method for converting aldoximes into nitriles. The dehydration occurs at 0 °C under very mild conditions by initial activation of the oxime oxygen, followed by treatment with a base and subsequent elimination of triphenylphosphine oxide. The substrate scope and functional group tolerance of this useful method are explored.
- Moussa, Ziad,Ahmed, Saleh A.,ElDouhaibi, Ahmad S.,Al-Raqa, Shaya Y.
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experimental part
p. 1826 - 1831
(2010/09/07)
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- Direct oxidative conversion of alcohols, amines, aldehydes, and benzyl halides into the corresponding nitriles with trichloroisocyanuric acid in aqueous ammonia
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A new and efficient procedure for the one-pot conversion of various alcohols, aldehydes and primary amines into the corresponding nitriles in excellent yields was easily achieved by trichloroisocyanuric acid (TCCA) as an oxidant and reagent in aqueous ammonia. Also, various benzylic halides were smoothly and directly converted into the corresponding aromatic nitriles in high yields under the same conditions. Georg Thieme Verlag Stuttgart New York.
- Veisi, Hojat
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experimental part
p. 2631 - 2635
(2010/09/08)
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- Bromodimethylsulfonium bromide (BDMS): a useful reagent for conversion of aldoximes and primary amides to nitriles
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An operationally simple and high yielding procedure has been developed for the preparation of nitriles from aldoximes and primary amides using bromodimethylsulfonium bromide (BDMS) as a novel and efficient reagent in the absence of any added base or catal
- Yadav, Lal Dhar S.,Srivastava, Vishnu P.,Patel, Rajesh
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experimental part
p. 5532 - 5535
(2010/01/11)
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- Poly(N,N′-dichloro-N-ethylbenzene-1,3-disulfonamide) and N,N,N′,N′-tetrachlorobenzene-1,3-disulfonamide as novel reagents for the synthesis of N-chloroamines, nitriles and aldehydes
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The applications of poly(N,N′-dichloro-N-ethylbenzene-1,3- disulfonamide) (PCBS) and N,N,N′,N′-tetrachlorobenzene-1,3- disulfonamide (TCBDA) as novel reagents for the preparation of N,N-dichloroamines, nitriles, and aldehydes from primary amines under various conditions are described. Also, a simple and effective procedure for the direct oxidative conversion of primary alcohols into nitriles was successfully carried out with TCBDA and PCBS in aqueous ammonia. Georg Thieme Verlag Stuttgart.
- Ghorbani-Vaghei, Ramin,Veisi, Hojat
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experimental part
p. 945 - 950
(2009/12/01)
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- Iodine/aqueous NH4OAc: An improved reaction system for direct oxidative conversion of aldehydes and alcohols into nitriles
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A convenient method for direct oxidative conversion of aldehydes and alcohols into nitriles has been developed by using the inexpensive and environmentally friendly reagent I2/aqueous NH4OAc. The aqueous NH4OAc as a non-toxic cyanide source is more eco-friendly than aqueous ammonia, because gaseous ammonia evaporates easily from aqueous ammonia but not from aqueous NH4OAc.
- Ren, Yi-Ming,Zhu, Yi-Zhong,Cai, Chun
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