- Aromatic nitration with nitric acid/trifluoromethanesulfonic anhydride
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Nitric acid/trifluoromethanesulfonic (triflic) anhydride was shown to be a highly effective electrophilic nitrating agent. A series of aromatics were nitrated under mild conditions in high yields. Similar results were also obtained when using nitric acid/
- Olah,Reddy,Prakash
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- An NMR study of the nitration of toluene over zeolites by HNO3-Ac2O
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Liquid and solid state NMR studies of the nitration of toluene with a mixture of nitric acid and acetic anhydride were performed in homogeneous solution and in a heterogeneous system using zeolite beta, mordenite, and ZSM-5 as catalysts. Instantaneous formation of acetyl nitrate occurred when nitric acid and acetic anhydride were mixed together but the reaction was not complete. The equilibrium constant for the reaction was ～ 5. Hydrolysis of acetic anhydride to acetic acid shifted the equilibrium back to the reactants, leading to nitric acid formation. The presence of this free nitric acid in the nitrating mixture acted as an acid catalyst during the nitration of toluene. The acetyl nitrate species was the effective nitrating species while isolated nitronium ions were not observed. Interaction of nitric acid with the zeolite led to strong bonding of the nitrate species to the framework aluminum, leading to a surface-bonded aluminum-nitrate complex. Heterogeneous zeolite-catalyzed nitration of toluene by acetyl nitrate improved the para- to ortho-nitrotoluene ratio compared to the homogeneous liquid phase nitration. The best para-selectivity was obtained with Al-beta and to a lesser extent with dealuminated mordenite, suggesting that the selectivity might be related to the presence of flexible lattice aluminum in these large pore zeolites.
- Prins,Kogelbauer,Haouas,Bernasconi
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- Nitrobenzyl Derivatives as Bioreductive Alkylating Agents: Evidence for the Reductive Formation of a Reactive Intermediate
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o- and p-nitrobenzyl chlorides and carbamates were chemically and electrochemically reduced in the presence and absence of the nucleophile morpholine; activation of these compounds by reduction was required to produce an intermediate capable of alkylation.The reduction products formed by the catalytic hydrogenation of each compound were examined by gas chromatography-mass spectrometry.In addition, the products generated by controlled-potential electrolysis were examined by ESR and NMR spectrometry.After a one-electron reduction, o- and p-nitrobenzyl chlorides were activated to the nitrobenzyl radicals, which subsequently dimerized to the dinitrobibenzyl derivatives or reacted with morpholine when present in the reaction medium to form the (nitrobenzyl)morpholine adducts.The nitrobenzyl carbamates were not activated after a one-electron reduction; however, the morpholine and the ether adducts of these agents were observed after catalytic hydrogenation.It was assumed that an intermediate or intermediates formed after the one-electron reduction product, or the full reduction product of the carbamates, were capable of alkylating various nucleophiles.Chemical reduction of the potential bioreductive alkylating agent (o-nitrobenzyl)-6-thioguanine produced (o-aminobenzyl)-6-thioguanine, indicating a lack of formation of a reactive electrophile by reduction. (o-, (m-, and (p-nitrobenzyl)-6-thioguanine analogues were also examined for cytotoxic activity toward EMT6 tumor cells under aerobic and hypoxic conditions.In agreement with the inability of (o-nitrobenzyl)-6-thioguanine to form a reactive species after chemical reduction, no decrease in the survival of neoplastic cells exposed to 10-4 M drug occurred under either aerobic or hypoxic conditions.
- Kirkpatrick, D. L.,Johnson, K. E.,Sartorelli, A. C.
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- SO42 -/ZrO2-titania nanotubes as efficient solid superacid catalysts for selective mononitration of toluene
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SO42 -/ZrO2-titania nanotubes-X (SO 42 -/ZrO2-TNTs-X; X of Ti/Zr) solid superacid catalysts with different atom ratios (Ti/Zr) were successfully prepared. The SO42 -/ZrO2-TNTs-2 (Ti/Zr of 2) have a specific surface area of 394 m2/g and an acid intensity of 1.839 mmol/g. The SO42 -/ZrO2-TNTs-2 show excellent selectivity (p/o of 3.34) and activity (yield of 98%) in the selective mononitration of toluene. Importantly, the SO42 -/ZrO2-TNTs-2 can be efficiently recycled and regenerated by simple sulfuric acid soaking.
- Chen, Pengfei,Du, Mingxing,Lei, He,Wang, Yan,Zhang, Guoliang,Zhang, Fengbao,Fan, Xiaobin
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- Application of H-ZSM-5 Zeolite for Regioselective Mononitration of Toluene
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The nitration of toluene with n-propyl nitrate has been carried out in the presence of H-ZSM-5 as the catalyst.Several H-ZSM-5 catalysts with different Si/Al ratios were investigated to determine the influence of varying Si/Al ratios on the catalytic activity.It was found that high Si/Al ratios enhanced the regioselectivity for the p-nitrotoluene over the ortho isomer under comparable conditions.The best o:m:p product distribution (5:0:95) was achieved using H-ZSM-5 with a Si/Al ratio of 1000.The isolable yield is 54percent.In contrast to conventional nitration methods, the product distribution reported in this study is remarkable.
- Kwok, Thomas J.,Jayasuriya, Keerthi,Damavarapu, Reddy,Brodman, Bruce W.
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- A PROCEDURE FOR QUANTITATIVE REGIOSELECTIVE NITRATION OF AROMATIC HYDROCARBONS IN THE LABORATORY
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Aromatic hydrocarbons are nitrated by metallic nitrates impregnated on the K10 montmorillonite in the presence of acetic anhydride (Menke conditions).The influence on this stoichiometric reaction of the conditions (metallic cation; solvent; temperature) i
- Cornelis, Andre,Delaude, Lionel,Gerstmans, Andre,Laszlo, Pierre
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- Some Aspects of Nitration of Aromatics by Lower Oxidation States of Nitrogen
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Nitration of benzene and toluene in trifluoroacetic acid (TFA) solution with sodium nitrite (N(III)) and nitrogen dioxide (N(IV)) occurs relatively slowly to produce mononitroarenes and oxidized byproducts.The yield of nitroarene improves as the ratio of
- Milligan, Barton
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- A PROCEDURE FOR QUANTITATIVE REGIOSELECTIVE NITRATION OF AROMATIC HYDROCARBONS IN THE LABORATORY
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Aromatic hydrocarbons are nitrated by metallic nitrates impregnated on the K10 montmorillonite in the presence of acetic anhydride (Menke conditions).The influence on this stoichiometric reaction of the conditions (metallic cation; solvent; temperature) i
- Cornelis, Andre,Delaude, Lionel,Gerstmans, Andre,Laszlo, Pierre
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- REGIOSELECTIVE LIQUID-PHASE TOLUENE NITRATION WITH MODIFIED CLAYS AS CATALYSTS
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Catalytic mononitration of toluene (yields of 50-81percent; turnover at least 850) occurs in the presence of modified clays with useful regioselectivities, such as (o:m:p) = 31:2:67.The nitrating species is extracted from concentrated nitric acid by carbo
- Cornelis, Andre,Gerstmans, Andre,Laszlo, Pierre
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- Regioselective catalyzed nitration of toluene by zeolites
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The nitration of toluene with nitric acid and nitrogen dioxide as nitration agent was studied. The effect of zeolite catalysts was also discussed. By using zeolite as catalysis, the yield of nitro-toluene was improved with nitric acid as nitration agent. The conversion of toluene and yield of nitro-toluene were both greatly enhanced with nitrogen dioxide as nitration agent.
- Dong, Xiongzi,Peng, Xinhua
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- Metal ion-exchanged bentonites as useful solid catalysts for regioselective nitration of toluene
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Metal ion-exchanged bentonites were found to be efficient catalysts in regioselective nitration of toluene when using nitric acid as nitrating agent. Fifteen metal ion-exchanged bentonites were tested as catalysts toward a para position considerably. Out of a range of catalysts tried silver-supported bentonite appeared of higher regioselectivity of ortho-para ratio of 0.64 in an acceptable yield of 45%. The possible recovery and reuse of catalyst suggest that system would be commercially viable.
- Zhang,Peng,Zhao
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- Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium
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Regardless of the sustainable development path, today, there are highly demanded chemical productions still operating that bear environmental and technological risks inherited from the previous century. The fabrication of nitro compounds, and nitroarenes in particular, is traditionally associated with acidic wastes formed in nitration reactions exploiting mixed acids. However, nitroarenes are indispensable for industrial and military applications. We faced the challenge and developed a greener, safer, and yet effective method for the production of nitroaromatics. The proposed approach comprises the application of an eco-friendly nitrating agent, namely dinitrogen pentoxide (DNP), in the medium of liquefied 1,1,1,2-tetrafluoroethane (TFE) - one of the most non-hazardous Freons. Importantly, the used TFE is not emitted into the atmosphere but is effortlessly recondensed and returned into the process. DNP is obtainedviathe oxidation of dinitrogen tetroxide with ozone. The elaborated method is characterized by high yields of the targeted nitro arenes, mild reaction conditions, and minimal amount of easy-to-utilize wastes.
- Fauziev, Ruslan V.,Kharchenko, Alexandr K.,Kuchurov, Ilya V.,Zharkov, Mikhail N.,Zlotin, Sergei G.
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p. 25841 - 25847
(2021/08/09)
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- Ultrathin Amorphous/Crystalline Heterophase Rh and Rh Alloy Nanosheets as Tandem Catalysts for Direct Indole Synthesis
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Heterogeneous noble-metal-based catalysis plays an essential role in the production of fine chemicals. Rh-based catalysts are one of the most active candidates for indole synthesis. However, it is still highly desired to develop heterogeneous Rh-based catalysts with high activity and selectivity. In this work, a general, facile wet-chemical method is reported to synthesize ultrathin amorphous/crystalline heterophase Rh and Rh-based bimetallic alloy nanosheets (NSs), including RhCu, RhZn, and RhRu. Impressively, the amorphous/crystalline heterophase Rh NSs exhibit enhanced catalytic activity toward the direct synthesis of indole compared to the crystalline counterpart. Importantly, the obtained amorphous/crystalline heterophase RhCu alloy NSs can further enhance the selectivity to indole of >99.9% and the conversion is 100%. This work demonstrates the importance of phase engineering and metal alloying in the rational design and synthesis of tandem heterogeneous catalysts toward fine chemical synthesis.
- Ge, Jingjie,Yin, Peiqun,Chen, Ye,Cheng, Hongfei,Liu, Jiawei,Chen, Bo,Tan, Chaoliang,Yin, Peng-Fei,Zheng, Hong-Xing,Li, Qiang-Qiang,Chen, Shuangming,Xu, Wenjie,Wang, Xiaoqian,Wu, Geng,Sun, Rongbo,Shan, Xiang-Huan,Hong, Xun,Zhang, Hua
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- Selective Mild Oxidation of Anilines into Nitroarenes by Catalytic Activation of Mesoporous Frameworks Linked with Gold-Loaded Mn3O4 Nanoparticles
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This work reports the synthesis and catalytic application of mesoporous Au-loaded Mn3O4 nanoparticle assemblies (MNAs) with different Au contents, i. e., 0.2, 0.5 and 1 wt %, towards the selective oxidation of anilines into the corresponding nitroarenes. Among common oxidants, as well as several supported gold nanoparticle platforms, Au/Mn3O4 MNAs containing 0.5 wt % Au with an average particle size of 3–4 nm show the best catalytic performance in the presence of tert-butyl hydroperoxide (TBHP) as a mild oxidant. In all cases, the corresponding nitroarenes were isolated in high to excellent yields (85–97 %) and selectivity (>98 %) from acetonitrile or greener solvents, such as ethyl acetate, after simple flash chromatography purification. The 0.5 % Au/Mn3O4 catalyst can be isolated and reused four times without a significant loss of its activity and can be applied successfully to a lab-scale reaction of p-toluidine (1 mmol) leading to the p-nitrotulene in 83 % yield. The presence of AuNPs on the Mn3O4 surface enhances the catalytic activity for the formation of the desired nitroarene. A reasonable mechanism was proposed including the plausible formation of two intermediates, the corresponding N-aryl hydroxylamine and the nitrosoarene.
- Armatas, Gerasimos S.,Daikopoulou, Vassiliki,Koutsouroubi, Eirini D.,Lykakis, Ioannis N.,Skliri, Euaggelia
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- The polyhedral nature of selenium-catalysed reactions: Se(iv) species instead of Se(vi) species make the difference in the on water selenium-mediated oxidation of arylamines
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Selenium-catalysed oxidations are highly sought after in organic synthesis and biology. Herein, we report our studies on the on water selenium mediated oxidation of anilines. In the presence of diphenyl diselenide or benzeneseleninic acid, anilines react with hydrogen peroxide, providing direct and selective access to nitroarenes. On the other hand, the use of selenium dioxide or sodium selenite leads to azoxyarenes. Careful mechanistic analysis and 77Se NMR studies revealed that only Se(iv) species, such as benzeneperoxyseleninic acid, are the active oxidants involved in the catalytic cycle operating in water and leading to nitroarenes. While other selenium-catalysed oxidations occurring in organic solvents have been recently demonstrated to proceed through Se(vi) key intermediates, the on water oxidation of anilines to nitroarenes does not. These findings shed new light on the multifaceted nature of organoselenium-catalysed transformations and open new directions to exploit selenium-based catalysis.
- Capperucci, Antonella,Dalia, Camilla,Tanini, Damiano
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supporting information
p. 5680 - 5686
(2021/08/16)
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- N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids
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Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.
- Budinská, Alena,Katayev, Dmitry,Passera, Alessandro,Zhang, Kun
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supporting information
(2020/03/30)
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- NITRATION
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The present invention relates to a process for preparing a nitrated compound, comprising the step of reacting a compound (A) comprising at least one substituted or unsubstituted aromatic or heteroaromatic ring, wherein said heteroaromatic ring comprises at least one heteroatom selected from the group consisting of oxygen, sulfur, phosphor, selenium and nitrogen, with a compound of formula (I) wherein Y is selected from the group consisting of hydrogen and nitro.
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Page/Page column 36; 41; 46; 64; 37; 47; 42; 65
(2020/05/28)
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- Hydrophobic WO3/SiO2 catalyst for the nitration of aromatics in liquid phase
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WO3/SiO2 solid acid catalyst synthesized using sol gel method has shown promising activity (up to 65% conversion) for aromatic nitration in liquid phase using commercial nitric acid (70%) as nitrating agent without using any sulfuric acid. The water formed during the reaction as well as water from dilute nitric acid (70%) was removed azeotropically, however due to the hydrophilic nature of the catalyst, some water gets strongly adsorbed on catalyst surface forming a barrier layer between catalyst and organics. This prevents effective adsorption of substrate on catalyst surface for its subsequent reaction. To improve the activity further, the hydrophilic/hydrophobic nature of the catalyst was altered by post modification by grafting with commercial short chain organosilane (Dynasylan 9896). The modified 20% WO3/SiO2 catalyst when used for o-xylene nitration in liquid phase, showed significant increase in the conversion from 65% to 80% under identical reaction conditions. Catalyst characterization revealed decrease in the surface area of 20% WO3/SiO2 from 356 m2/g to 302 m2/g after grafting with Dynasylan 9896. The fine dispersion of WO3 particles (2–5 nm) on silica support was not affected due to modification. NMR and FTIR study revealed the decrease in surface hydroxyl groups imparting hydrophobicity to the catalyst. Interestingly the total acidic sites of the catalyst remained almost unaltered (0.54 mmol NH3/g) even after modification. Even though, the acidity and other characteristics of the catalyst did not change appreciably, there was a considerable increase in the o-xylene conversion which can be ascribed to the hydrophobic nature of the catalyst.
- Kulal,Kasabe,Jadhav,Dongare,Umbarkar
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p. 105 - 113
(2019/02/15)
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- 2-Methyl-1,3-disulfoimidazolium polyoxometalate hybrid catalytic systems as equivalent safer alternatives to concentrated sulfuric acid in nitration of aromatic compounds
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Ionic liquid-derived polyoxometalate salts [mdsim]3[PM12O40] (where M?=?W and Mo) of two heteropolyacids H3PW12O40.nH2O and H3PMo12O40.nH2O were synthesized using 2-methyl-1,3-disulfoimidazolium chloride ([mdsim][Cl]) ionic liquid and the corresponding heteropolyacids. Three equivalents of [mdsim][Cl] were treated with the respective Keggin-structured heteropolyacids (one equivalent) in aqueous medium at room temperature to afford the water-stable ionic polyoxometalates as acidic solids. They were completely characterized using spectroscopic and other analytical techniques including thermal analysis and Hammett acidity studies. The inherent Br?nsted acidic properties of ─SO3H group of these polyoxometalate salts were studied for the nitration of aromatic compounds with 69% HNO3 at normal temperature and 80°C without use of any external concentrated sulfuric acid. These strongly acidic polyoxometalates display good recyclability and efficient reusability.
- Saikia, Susmita,Borah, Ruli
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- A convenient room temperature ipso-nitration of arylboronic acid catalysed by molecular iodine using zirconium oxynitrate as nitrating species: An experimental and theoretical investigation
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A simple and convenient protocol has been developed for ipso-nitration of arylboronic acid catalysed by molecular iodine at room temperature, using zirconium oxynitrate as the nitrating species. The protocol is applicable to electronically diverse aryl- and heteroarylboronic acid moieties under mild reaction conditions with good to excellent isolated yields. Furthermore, a theoretical investigation has been performed for the same reaction, and reaction profiles are modelled using modern density functional theory (DFT). DFT-based results support the experimentally observed results.
- Mahanta, Abhijit,Gour, Nanda Kishor,Sarma, Plaban Jyoti,Borah, Raju Kumar,Raul, Prasanta Kumar,Deka, Ramesh Chandra,Thakur, Ashim Jyoti,Bora, Utpal
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- On/Off O2 Switchable Photocatalytic Oxidative and Protodecarboxylation of Carboxylic Acids
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Photoredox catalysis in recent years has manifested a powerful branch of science in organic synthesis. Although merging photoredox and metal catalysts has been a widely used method, switchable heterogeneous photoredox catalysis has rarely been considered. Herein, we open a new window to use a switchable heterogeneous photoredox catalyst which could be turned on/off by changing a simple stimulus (O2) for two opponent reactions, namely, oxidative and protodecarboxylation. Using this strategy, we demonstrate that Au@ZnO core-shell nanoparticles could be used as a switchable photocatalyst which has good catalytic activity to absorb visible light due to the localized surface plasmon resonance effect of gold, can decarboxylate a wide range of aromatic and aliphatic carboxylic acids, have multiple reusability, and are a reasonable candidate for synthesizing both aldehydes/ketones and alkane/arenes in a large-scale set up. Some biologically active molecules are also shown via examples of the direct oxidative and protodecarboxylation which widely provided pharmaceutical agents.
- Bazyar, Zahra,Hosseini-Sarvari, Mona
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p. 13503 - 13515
(2019/10/11)
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- Preparation method of substituted nitrobenzene compound
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The invention discloses a preparation method of a substituted nitrobenzene compound. The method comprises the following steps: carrying out a decarboxylation reaction as shown below on a compound II under the action of alkali in a solvent at the temperature of 150 to 250 DEG C to obtain a compound I; the alkali is one or more of carbonates and bicarbonates of alkali metals. Compared with some metal-catalyzed decarboxylation methods, the preparation method of the substituted nitrobenzene compound has the advantages of simple operation, low production cost, convenient post-treatment and high yield, and more application values in industrial production.
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Paragraph 0026-0029
(2019/03/29)
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- Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters
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A method for the direct methylation of aryl, heteroaryl, and vinyl boronate esters is reported, involving the reaction of iodomethane with aryl-, heteroaryl-, and vinylboronate esters catalyzed by palladium and PtBu2Me. This transformation occurs with a remarkably broad scope and is suitable for late-stage derivatization of biologically active compounds via the boronate esters. The unique capabilities of this method are demonstrated by combining carbon-boron bond-forming reactions with palladium-catalyzed methylation in a tandem transformation.
- Haydl, Alexander M.,Hartwig, John F.
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supporting information
p. 1337 - 1341
(2019/02/26)
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- Silica-supported perchloric acid and potassium bisulfate as reusable green catalysts for nitration of aromatics under solvent-free microwave conditions
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Silica-supported perchloric acid and bisulfate (SiO2/HClO4 and SiO2/KHSO4) have been developed as reusable green catalysts for nitration of aromatic compounds using NaNO2 in acetonitrile medium under conventional and solvent-free microwave conditions. The reaction times under microwave irradiation are significantly shorter than conventional method even though the yields obtained in microwave-assisted reactions are comparable with those obtained under reflux conditions.
- Kumar, M. Satish,Sriram, Y. Hemanth,Venkateswarlu,Rajanna,Sudhakar, M. Sai,Venkanna, Purugula,Saiprakash
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supporting information
p. 59 - 67
(2017/12/26)
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- Aerobic oxidations with N-hydroxyphthalimide in trifluoroacetic acid
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The potential of highly polar trifluoroacetic acid as a media for the metal-free aerobic oxidations propagated by phthalimide N-oxyl- (PINO) radical was demonstrated experimentally utilizing N-hydroxyphthalimide (NHPI) as a catalyst and HNO3 or NaNO2 as promoters. The oxidations of toluene, cyclohexane, adamantane, diamantane, and 3-oxadiamantane gave, respectively, benzaldehyde, adipic acid, 1-hydroxyadamantane, 1-hydroxydiamantane, and 9-hydroxy-3-oxadiamantane with up to 90% selectivities under high conversions of starting material. From the density functional theory computations at the M06-2X and B3LYP-D3 levels the polarized transition structures (TS) for the hydrogen abstraction from toluene and benzyl alcohol with highly electrophilic PINO-radical are substantially stabilized by non-covalent interactions (π–π stacking). Such additional stabilization is not present in the TS for the H-abstraction from benzaldehyde thus retarding its over-oxidation to benzoic acid.
- Gunchenko, Pavel A.,Li, Jing,Liu, Bifu,Chen, Hongyan,Pashenko, Alexander E.,Bakhonsky, Vladyslav V.,Zhuk, Tatyana S.,Fokin, Andrey A.
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- Method for nitrating aromatic compound by using nitrate under the action of auxiliary agent
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The invention discloses a method for nitrating an aromatic compound by using a nitrate under the action of an auxiliary agent, and provides an aromatic nitro compound preparation method, which comprises: in the presence of an external action and an auxiliary agent, carrying out a nitrating reaction on an aromatic compound and a metal nitrate or a hydrate thereof to obtain the aromatic nitro compound, wherein the external action can cause the physical and/or chemical property change of a substance, the auxiliary agent is a substance having water absorbing ability, the external action can be mechanical force or heating, and the mechanical force can be any one selected from compression, shearing, impacting, friction, stretching, bending and vibration. According to the present invention, the method does not require any solvents so as to avoid the generation of the waste liquid; the acidic substance is not used, such that the treatment is simple after the reaction is completed, and the equipment is not damaged; the added auxiliary agent can be theoretically recycled; and the method has extremely high conversion rate and extremely high selectivity, and can be used for the nitration of conventional aromatic compounds.
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Paragraph 0071; 0072; 0090; 0091
(2018/09/11)
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- Mechanical force under the action of the nitration of aromatic compounds of nitrate method (by machine translation)
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The invention discloses a mechanical force under the action of the nitration of aromatic compounds of nitrate method. The invention provides a method for preparing aromatic nitro compounds, comprising the following steps: under the action of mechanical force, aromatic compound with a metal nitrate or its hydrate by the nitration reaction, to obtain the aromatic nitro compound; the mechanical fastener is machinery offers can cause material physical and/or chemical nature of the change of the external force. The mechanical force can be compression, shear, impact, friction, tensile, bending and vibration of any kind. The invention has the following advantages: without the use of any solvent, thereby avoiding the waste liquid produced; and without the use of the acidic substance, the reaction is complete after treatment is simple, without any damage to the apparatus; a very high conversion and selectivity, can be applied to the nitration of conventional aromatic compound. (by machine translation)
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Paragraph 0056; 0057; 0085; 0086
(2018/09/11)
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- Complexes of copper(I) with aromatic compounds facilitate selective electrophilic aromatic substitution
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We report on the selective formation of ortho-nitrophenol, ortho-nitrotoluene (1-Methyl-2-nitrobenzene) and ortho-phenolsulfonic acid (2-Hydroxybenzenesulfonic acid) through reaction of the Cu(I)-aromatic ring complex of phenol or toluene. In the case of nitration of phenol, the reaction could be formulated as: (Figure presented.) The copper(I)-aromatic ring complex is formed in situ from Cu(II) and metallic copper in deaerated aqueous solutions containing the aromatic compounds. Phenol or toluene shift the comproportionation reaction of copper(0) and copper(II) towards the formation of Cu(I): (Formula presented.) The stability constant of Cu(I)-phenol in aqueous solutions was reported previously as 900 ± 100 M?1. The surprisingly stable d?π* Cu(I)-phenol complex causes distortion of the ring structure which facilitates selective substitutions. Similar results are reported for sulfonation of phenol (in aqueous solutions) and for nitration and sulfonation of toluene in a two phase process.
- Saphier, Magal,Levitsky, Inna,Masarwa, Alexandra,Saphier, Oshra
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p. 1738 - 1748
(2018/10/24)
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- Decarboxylative Benzylation of Aryl and Alkenyl Boronic Esters
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The copper-catalyzed decarboxylative benzylation of aryl and alkenyl boronic esters with electron-deficient aryl acetates is reported. The oxidative coupling proceeds under mild, aerobic conditions and tolerates a host of potentially reactive electrophilic functional groups that would be problematic with traditional benzylation methods (aryl iodides and bromides, protic heteroatoms, aldehydes, Michael acceptors). A reaction pathway in which a benzylic nucleophile is generated by aryl acetate decarboxylation and in turn is intercepted by the catalyst to form diarylmethane products is supported by mechanistic studies.
- Moon, Patrick J.,Fahandej-Sadi, Anis,Qian, Wenyu,Lundgren, Rylan J.
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supporting information
p. 4612 - 4616
(2018/03/26)
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- Ipso-nitration of arylboronic acids with copper nitrate and trifluoroace-tic acid
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An efficient and novel nitrating reagent has been developed for ipso-nitration of arylboronic acids. By using inexpensive and commercially available Cu(NO3)2/CF3COOH as nitrating reagent, various nitroarenes are produced in moderate to excellent yields (51-96%). Advantages of this procedure are the operational simplicity and no need of extra catalyst.
- Wang, Zhu-Qing,Guo, Meng-Ping,Wen, Yong-Ju,Shen, Xiu-Li,Lv, Mei-Yun,Zhou, Xiu-Ling
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p. 891 - 894
(2018/11/06)
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- Fluoropolymer-Coated PDMS Microfluidic Devices for Application in Organic Synthesis
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In recent years there has been huge interest in the development of microfluidic reactors for the synthesis of small molecules and nanomaterials. Such reaction platforms represent a powerful and versatile alternative to traditional formats since they allow for the precise, controlled, and flexible management of reactive processes. To date, the majority of microfluidic reactors used in small-molecule synthesis have been manufactured using conventional lithographic techniques from materials such as glasses, ceramics, stainless steel, and silicon. Surprisingly, the fabrication of microfluidic devices from such rigid materials remains ill-defined, complex, and expensive. Accordingly, the microfluidic toolkit for chemical synthesis would significantly benefit from the development of solvent-resistant microfluidic devices that can be manufactured using soft-lithographic prototyping methods. Whilst significant advances in the development of solvent-resistant polymers have been made, only modest steps have been taken towards simplifying their use as microfluidic reactors. Herein, we emphasize the benefits of using a commercially available, amorphous perfluorinated polymer, CYTOP, as a coating with which to transform PDMS into a chemically inert material for use in organic synthesis applications. Its efficacy is demonstrated through the subsequent performance of photooxidation reactions and reactions under extremely acidic or basic conditions.
- Yang, Tianjin,Choo, Jaebum,Stavrakis, Stavros,de Mello, Andrew
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p. 12078 - 12083
(2018/08/21)
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- Sulfated SO4 2?/WO3 as an efficient and eco-friendly catalyst for solvent-free liquid phase nitration of toluene with NO2
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With the increase in environmental awareness, developing a highly efficient and environmentally benign nitration process has very important academic and applied industrial values in the synthesis of nitro-compounds. Towards this goal, we have developed an efficient and environmentally friendly approach for solvent-free liquid phase nitration of toluene by employing NO2 as a nitrating agent and sulfated SO4 2?/WO3 as a catalyst replacing traditional nitric acid–sulfuric acid under mild conditions. The results indicate that SO4 2?/WO3 as an effective and eco-friendly catalyst exhibits excellent catalytic activity and reusability for the nitration of toluene with NO2. In addition, the possible pathway for liquid phase nitration of toluene with NO2 over sulfated SO4 2?/WO3 catalyst was suggested. The present method makes this nitration process safe and environmentally friendly, and has the potential to enable a sustainable production of nitro-compounds from the liquid phase nitration of aromatic hydrocarbon with NO2 in industrial applications.
- Jiao, Yinchun,Zhu, Man,Deng, Renjie,Jian, Jian,Yin, Yi,You, Kuiyi
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p. 3961 - 3974
(2017/06/20)
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- Convenient, metal-free ipso-nitration of arylboronic acids using nitric acid and trifluoroacetic acid
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A feasible protocol for the direct ipso-nitration of arylboronic acids using trifluoroacetic acid and nitric acid as nitration reagent has been developed. Various aromatic nitro compounds are produced in moderate to good yields under the metal-free conditions. The method is operationally simple and regioselective, and might have potential application in industry.
- Shen, Guodong,Zhao, Lingyu,Liu, Wanxing,Huang, Xianqiang,Song, Huina,Zhang, Tongxin
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supporting information
p. 10 - 14
(2016/12/30)
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- NH4I/tert-butyl hydroperoxide-promoted oxidative C–N cleavage of tertiary amines leading to nitroaromatic compounds
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A NH4I/tert-butyl hydroperoxide-promoted oxidation of tertiary N-aryl-N,N-dialkylamines in DMSO has been developed to access nitroaromatic compounds. This methodology involves sequential N-dealkylation reactions in one-pot and a radical pathway is proposed.
- Shao, Ying,Zheng, Hao,Wu, Zhuhong,Huang, Lei,Tong, Jingjing,Wu, Ming,Sun, Xiaoqiang
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p. 504 - 508
(2017/10/03)
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- N-Trifluoromethylation of Nitrosoarenes with Sodium Triflinate
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A highly efficient N-trifluoromethylation of nitrosoarenes is reported. The inexpensive and convenient Langlois reagent (sodium triflinate) is employed as a CF3-radical source in combination with a copper catalyst and an oxidant. N-Trifluoromethylated hydroxylamines are obtained in high yields within 1 h at room temperature. The addition of hydroquinone was found to be instrumental to prevent the formation of side products. The method is high-yielding, is scalable, and displays a high functional group tolerance.
- Van der Werf, Angela,Hribersek, Matic,Selander, Nicklas
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supporting information
p. 2374 - 2377
(2017/05/12)
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- Regioselective mononitration of aromatic compounds with N2O5 by acidic ionic liquids via continuous flow microreactor
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We employed N2O5 as highly active nitrating reagents and a host of acidic ionic liquid as catalysts in these reactions which were conducted in a continuous flow microreactor. When we utilized PEG400-DAIL as catalysts, the conversion of toluene was increased to 95.5 % and the yield of mononitration product (o/p ratio reached 1.10) significantly improved to 99 %, meanwhile the reaction time was drastically shortened to 1/120 of the conventional reactor. Nitration in ionic liquids was surveyed using a host of aromatic substrates with similar reactivity. The ionic liquid recycling procedures had also been devised.
- Liu, Jianhua,Li, Bindong,Wang, Huan
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p. 513 - 516
(2016/01/20)
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- NITRATION OF AROMATIC COMPOUNDS
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The present invention provides a process for nitrating aromatic compounds without the need for a solid catalyst and/or any organic solvents and/or any other additives. A typical process includes combining or admixing a nitric acid and an anhydride compound under conditions sufficient to produce a reactive intermediate. The aromatic compound to be nitrated is then added to this reactive intermediate to produce a nitroaromatic compound. The nitroaromatic compound can be substituted with one or more, typically, one to three, and often one or two nitrate (-NO2) groups.
- -
-
Paragraph 0049; 0050
(2016/08/17)
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- Enantioselective Total Syntheses of (-)-Rhazinilam, (-)-Leucomidine B, and (+)-Leuconodine F
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A divergent total synthesis of three structurally distinct natural products from imine 9 was accomplished through an approach featuring: 1) a Pd-catalyzed decarboxylative cross-coupling, and 2) heteroannulation of 9 with bromoacetaldehyde and oxalyl chloride to give tetrahydroindolizine 6 and dioxopyrrole 7, respectively. The former was converted into (-)-rhazinilam, while the latter was converted into (-)-leucomidine B and (+)-leuconodine F. A substrate-directed highly diastereoselective reduction of a sterically unbiased double bond by using a homogeneous palladium catalyst was developed. A self-induced diastereomeric anisochronism (SIDA) phenomenon was observed for leucomidine B. Be divergent: Concise total syntheses of (-)-rhazinilam, (-)-leucomidine B, and (+)-leuconodine F were accomplished from the common intermediate A. A homogeneous palladium catalyst was exploited for the first time to accomplish a substrate-directed highly diastereoselective hydrogenation of a sterically unbiased double bond. A self-induced diastereomeric anisochronism (SIDA) phenomenon was observed for leucomidine B.
- Dagoneau, Dylan,Xu, Zhengren,Wang, Qian,Zhu, Jieping
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supporting information
p. 760 - 763
(2016/02/27)
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- A simple protocol for Cu-catalyzed protodecarboxylation of (hetero)aromatic carboxylic acids
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A simple and practical protodecarboxylation of o-nitrobenzoic acids as well as heteroaromatic carboxylic acids with various substituents via using CuI/Et3N has been established. This transformation provides a viable and low-cost approach to generating previously unavailable substituted arenes from readily accessible aryl carboxylic acids as the starting materials.
- Li, Zhaojie,Fu, Zhengjiang,Zhang, Haixia,Long, Jiao,Song, Yuanyuan,Cai, Hu
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supporting information
p. 3014 - 3018
(2016/05/09)
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- N-methyl-2-chloropyridinium iodide/NaNO2/Wet SiO2: Neutral reagent system for the nitration of activated aromatic compounds under very mild conditions
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Mononitration of activated aromatic compounds using N-methyl-2-chloro-pyridinium iodide (Mukaiyama reagent)/NaNO2/wet SiO2 reagent system under neutral, very mild and environmentally safer reaction condition has been developed. Various structurally diverse aromatic rings are subjected in this condition and the corresponding nitro-aromatic compounds are prepared in moderately high yields.
- Azadi, Roya,Nazari-Far, Zahra
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p. 136 - 140
(2015/06/22)
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- Copper-cobalt synergy in Cu1-xCoxFe2O4 spinel ferrite as a highly efficient and regioselective nanocatalyst for the synthesis of 2,4-dinitrotoluene
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Highly regioselective dinitration of toluene with nitric acid as nitrating agent in the presence of Cu1-xCoxFe2O4 (0 ≤ x ≤ 1) as nanocatalysts is described. The results of this protocol show that this nitration system can significantly improve the selectivity and the yield of 2,4-dinitrotoluene. The prepared spinel ferrites were characterized by scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), and Fourier transform infrared spectroscopy (FT-IR). Copper and cobalt synergy (50%:50%) in spinel ferrite also shows the best catalytic activity in the selectivity of dinitrotoluene under solvent-free conditions.
- Fareghi-Alamdari, Reza,Zandi, Farzad,Keshavarz, Mohammad Hossein
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p. 71911 - 71921
(2015/09/08)
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- A novel transition metal free [bis-(trifluoroacetoxy)iodo]benzene (PIFA) mediated oxidative ipso nitration of organoboronic acids
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A mild, convenient and transition metal free methodology for oxidative ipso nitration of diversely functionalized organoboronic acids, including heteroaryl- and alkylboronic acids, has been developed at ambient temperature using a combination of [bis-(trifluoroacetoxy)]iodobenzene (PIFA) - N-bromosuccinimide (NBS) and sodium nitrite as the nitro source. It is anticipated that the reaction proceeds through in situ generation of NO2 and O-centred organoboronic acid radicals followed by the formation of an O-N bond via combination of the said radicals. Finally transfer of the NO2 group to the aryl moiety occurs through 1,3-aryl migration to provide the nitroarenes.
- Chatterjee, Nachiketa,Bhatt, Divya,Goswami, Avijit
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supporting information
p. 4828 - 4832
(2015/05/05)
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- Heterogeneous photocatalytic C-C coupling: Mechanism of plasmon-mediated reductive dimerization of benzyl bromides by supported gold nanoparticles
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The use of gold nanoparticles supported on TiO2 (Au@TiO2) as photocatalysts was extended to include photoinduced reductive C-C coupling. Surface plasmon excitation of supported AuNPs in the presence of an amine leads to the C-C coupling of a variety of substituted benzyl bromides at room temperature with good yields in a free radical-mediated reaction. The overall efficiency of the C-C coupling is largely dependent on the nature of the amine used.
- Lanterna, Anabel E.,Elhage, Ayda,Scaiano, Juan C.
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p. 4336 - 4340
(2015/09/01)
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- Para-Selective Halogenation of Nitrosoarenes with Copper(II) Halides
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The para-selective direct bromination and chlorination of nitrosoarenes with copper(II) bromide and chloride is reported. Under mild reaction conditions, a range of halogenated arylnitroso compounds are obtained in moderate to good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of a one-pot procedure to obtain the corresponding para-halogenated aniline- and nitrobenzene derivatives.
- Van Der Werf, Angela,Selander, Nicklas
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supporting information
p. 6210 - 6213
(2016/01/09)
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- Hazardous o-toluidine mineralization by photocatalytic bismuth doped ZnO slurries
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Photocatalytic mineralization of o-toluidine in aqueous media under UV/solar irradiation was achieved by bare and bismuth doped zinc oxide nanoparticles. By adopting different analytical approaches a reaction mechanism is proposed, explaining the differences in photodetoxification performances.
- Cappelletti,Pifferi,Mostoni,Falciola,Di Bari,Spadavecchia,Meroni,Davoli,Ardizzone
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supporting information
p. 10459 - 10462
(2015/06/25)
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- On the performance and mechanisms of toluene removal by FeOx/SBA-15-assisted non-thermal plasma at atmospheric pressure and room temperature
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FeOx/SBA-15 catalysts were prepared via impregnation and utilized for toluene removal in dielectric barrier discharge (DBD) plasma at atmospheric pressure and room temperature. Toluene removal was investigated in the environment of various mixed N2/O2 plasmas, showing that toluene removal efficiency and COx selectivity were greatly increased by FeOx/SBA-15 and that the organic intermediates were greatly reduced by catalysts. In pure N2 plasma, the bulk oxygen in the catalyst was involved in the toluene oxidation, and the 3%FeOx/SBA-15 catalyst showed the optimal toluene oxidation activity. The catalysts were characterized by scanning electron microscopy (SEM), X-ray diffraction (XRD), N2 adsorption-desorption, X-ray photoelectron spectroscopy (XPS), H2 temperature-programmed reduction (H2-TPR) and O2 temperature-programmed desorption (O2-TPD), showing that toluene oxidation was closely related to the highly dispersed nature of iron on the SBA-15 surface, the reduction temperature of Fe2+ and the oxygen adsorption ability of the catalyst. The pathways of toluene decomposition in the combination of FeOx/SBA-15 with a non-thermal plasma (NTP) system were proposed based on the identified intermediates.
- Lu, Meijuan,Huang, Rong,Wu, Junliang,Fu, Mingli,Chen, Limin,Ye, Daiqi
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p. 274 - 286
(2015/02/19)
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- Competition between electron-donor and electron-acceptor substituents in nitrotoluene isomers: A photoelectron spectroscopy and ab initio investigation
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We present an investigation of the close relationship between chemical structure, physical properties and reactivity of the three nitrotoluene isomers: a joint experimental and theoretical study, based on X-ray photoelectron spectroscopy (XPS) measurements and ab initio calculations, addressing the complex interplay between the competing electron-donor and electron-acceptor effects of the nitro- and methyl-substituents on the chemical properties of the nitrotoluene isomers. As the main results of the investigation we: (i) point out that accurate ab initio calculations play a key role in the complete assignment of photoemission measurements, as well as in the estimate of proton affinities in the case of all the eligible sites; (ii) revisit, at a more quantitative level, textbook models based on inductive and resonant effects of different substituents of the aromatic ring, as well as on the hyper-conjugative connection of the methyl group to the π-conjugated system; (iii) provide an accurate analysis of correlation patterns between calculated proton affinities and core-ionization energies, which represent a powerful tool, capable of predicting site-specific reactivities of polysubstituted molecules in the case of electrophilic aromatic substitution reactions.
- Rondino, Flaminia,Catone, Daniele,Mattioli, Giuseppe,Bonapasta, Aldo Amore,Bolognesi, Paola,Casavola, Anna Rita,Coreno, Marcello,O'Keeffe, Patrick,Avaldi, Lorenzo
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p. 5272 - 5282
(2014/01/23)
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- Regioselective dinitration of simple aromatics over zeolite Hβ/nitric acid/acid anhydride systems
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Various nitration systems comprising nitric acid, acid anhydride and zeolite H￡] in the absence of solvent are described. Direct double nitration of toluene with a nitric acid, propanoic anhydride and zeolite Hβ system has been developed to give 2,4-dinitrotoluene in 98% yield, with a 2,4-:2,6-dinitrotoluene ratio of 123:1. This system also nitrates activated mono-substituted benzenes (anisole and phenetole) and moderately activated mono-substituted benzenes (ethylbenzene and propylbenzene) to give mainly 2,4-dinitro derivatives. The zeolite can be recovered, regenerated and reused to give almost the same yield as that given when fresh zeolite is used. ARKAT-USA, Inc.
- Smith, Keith,Alotaibi, Mohammad Hayal,El-Hiti, Gamal A.
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p. 107 - 123
(2014/04/17)
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- Bismuth triflate catalyzed mononitration of aromatic compounds with N 2O5
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This page isvestigated that bismuth triflate catalysed the nitration of a range of simple aromatic compounds in good to excellent yields at 0-30 °C within 2 h using N2O5 and the catalyst can be recycled without apparent loss of activity. Mechanistic insights demonstrate that triflic acid is generated and that, at least, when two competing catalytic cycles are operating at the same time: a rapid one involving triflic acid and a slower one involving the bismuth triflate.
- Qian, Hua,Wang, Ya,Liu, Dabin,Lv, Chunxu
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p. 509 - 512
(2014/05/20)
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- Regioselective preparation of 4-nitro-o-xylene using nitrogen dioxide/molecular oxygen over zeolite catalysts. remarkable enhancement of para-selectivity
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In the presence of molecular oxygen and zeolite H-β with Si/Al 2 = 500, o-xylene reacted regioselectively with liquid nitrogen dioxide at 35 °C to yield mononitro-o-xylenes as the main product, where the 4-nitro-o-xylene isomer predominated up to 89% and the 4-nitro-/3-nitro-o- xylene isomer ratio improved to 7.8. The process is eco-friendly, less expensive, and the zeolite could be easily regenerated by a simple workup to afford results similar to those obtained with the fresh catalyst.
- Liu, Hongtao,Ji, Cheng,Dong, Xiongzi,Peng, Xinhua,Shi, Chunjie
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supporting information
p. 817 - 819
(2014/06/23)
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- Phosphoric acid modified montmorillonite clay: A new heterogeneous catalyst for nitration of arenes
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The easily available montmorillonite clay is treated with phosphoric acid and 10 wt.% is found to be the optimum concentration of phosphoric acid that can be adsorbed chemically on the surface of the clay. Acidity of this phosphoric acid treated montmorillonite clay (PAM) is determined by volumetric as well as potentiometric titration and characterized. Catalytic efficacy of PAM in nitration of various aromatic compounds is reported.
- Bharadwaj, Saitanya K.,Boruah, Purna K.,Gogoi, Pradip K.
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p. 124 - 128
(2014/12/11)
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- Aldehydes and ketones formation: Copper-catalyzed aerobic oxidative decarboxylation of phenylacetic acids and α-hydroxyphenylacetic acids
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Aromatic aldehydes or ketones from copper catalyzed aerobic oxidative decarboxylation of phenylacetic acids and α-hydroxyphenylacetic acids have been synthesized. This reaction combined decarboxylation, dioxygen activation, and C-H bond oxidation steps in a one-pot protocol with molecular oxygen as the sole terminal oxidant. This reaction represents a novel decarboxylation of an sp3-hybridized carbon and the use of a benzylic carboxylic acid as a source of carbonyl compounds.
- Feng, Qiang,Song, Qiuling
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p. 1867 - 1871
(2014/03/21)
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- Preparation of heteropoly acid based amphiphilic salts supported by nano oxides and their catalytic performance in the nitration of aromatics
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A series of Keggin heteropoly acid anion based amphiphilic salts supported by nano oxides were synthesized and used as catalysts in the nitration of aromatic compounds with HNO3. The reaction conditions in the nitration of toluene were optimized and both 92.6% conversion and good para selectivity (ortho:para = 1.09) were obtained.
- Wang, Peng-Cheng,Yao, Kai,Lu, Ming
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p. 2197 - 2202
(2013/03/14)
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- Preparation, catalytic performance and theoretical study of porous sulfated binary metal oxides shell (SO42 -/M1xO y-M2xOy) using pollen grain templates
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Porous micro-sized particles of binary metal oxide (SO4 2 -/M1xOy-M2xOy) shell were prepared by template-directed synthesis method employing HCl-treated pollen grains. With 150 m2/g high surface area, these solid acids could provide more acid sites and thus obtain better catalytic activity. Using aromatic nitration as the typical reaction, their catalytic performances were evaluated and showed a significant improvement in both conversion and regioselectivity. Then, with chlorobenzene as substrate, theoretical studies were performed to investigate the interaction between transition metals and chlorobenzene. The results showed that the excellent para-selectivity was closely relative to the metal ion in these solid acids.
- Wang, Peng Cheng,Yao, Kai,Zhu, Jie,Liu, Xiang,Lu, Ting Ting,Lu, Ming
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-
- Design, synthesis and anticancer activity evaluation of diazepinomicin derivatives
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A series of diazepinomicin derivatives were synthesized and evaluated in vitro for their growth inhibitory activity against the human carcinoma cell lines. The results indicated the anticancer selectivity of this kind of compounds. Based on the results, preliminary structure-activity relationships were discussed.
- Yu, Yongguo,Wu, Jianbo,Lei, Fan,Chen, Lei,Wan, Weili,Hai, Li,Guan, Mei,Wu, Yong
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p. 369 - 373
(2013/07/26)
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- Novel biphenyl organocatalysts for iminium ion-catalyzed asymmetric epoxidation
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Two novel chiral biphenyl iminium salts derived from L-acetonamine, containing electron-withdrawing 3,30-substituents on the biphenyl unit, have been prepared and tested as asymmetric catalysts for epoxidation of prochiral alkenes. The results are compared with those achieved using the corresponding unsubstituted system.
- Farah, Mohamed M.,Page, Philip C. Bulman,Buckley, Benjamin R.,Blacker, A. John,Elsegood, Mark R.J.
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p. 758 - 769
(2013/07/27)
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- Recyclable nanoscale copper(I) catalysts in ionic liquid media for selective decarboxylative C-C bond cleavage
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Here we report the synthesis and application of finely divided Cu 2O nanoparticles (Cu2O-NPs) in the range from 5.5 nm to 8.0 nm in phosphonium ionic liquids as the first recyclable and effective catalytic system for smooth, ligand- and additive-free protodecarboxylation of 2-nitrobenzoic acid as a model substrate and further derivatives. The reactions run with low catalyst loadings and result in quantitative yield in ten consecutive recycling experiments. In addition this system is highly selective towards electron-poor 2-nitrobenzoic acids.
- Kessler, Michael T.,Gedig, Christian,Sahler, Sebastian,Wand, Patricia,Robke, Silas,Prechtl, Martin H. G.
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p. 992 - 1001
(2013/04/24)
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- Aromatic nitration under neutral conditions using N-bromosuccinimide/ silver(I) nitrate
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The use of N-bromosuccinimide and silver nitrate as a convenient reagent system for the nitration of aromatic compounds under neutral and environmentally safer reaction conditions is described.
- Nowrouzi, Najmeh,Mehranpour, Abdol Mohammad,Bashiri, Elham,Shayan, Zohre
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experimental part
p. 4841 - 4842
(2012/09/22)
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- Rare earth metal triflates catalyzed electrophilic nitration using N 2O5
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A mild, efficient and eco-friendly process for the electrophilic nitration is described using N2O5 as a green nitrating agent in the presence of rare earth metal triflates [RE(OTf)3] under mild conditions.
- Ma, Xiao Ming,Li, Bin Dong,Lu, Ming,Lv, Chun Xu
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experimental part
p. 73 - 76
(2012/03/26)
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