cas 577-19-5, 1-Bromo-2-nitrobenzene | Articles data

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Nitration of deactivated aromatic compounds via mechanochemical reaction
A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.
Wu, Jian-Wei,Zhang, Pu,Guo, Zhi-Xin
supporting information

(2021/05/05)

Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium
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.
p. 25841 - 25847
(2021/08/09)

Low-temperature and highly efficient liquid-phase catalytic nitration of chlorobenzene with NO2: Remarkably improving the para-selectivity in O2-Ac2O-Hβ composite system
In this work, we developed a low-temperature and efficient approach for the highly selective preparation of valuable p-nitrochlorobenzene from the liquid-phase catalytic nitration of chlorobenzene with NO2 in O2-Ac2O-Hβ composite system. The results demonstrated that the introduction of molecular oxygen remarkably enhanced the chlorobenzene conversion and the cooperation catalysis of Hβ zeolite and Ac2O envidently improved the selectivity to para-nitro product. Under the optimized reaction conditions, 93.6 % of the selectivity to p-nitrochlorobenzene with 84.0 % of chlorobenzene conversion was obtained, and the ratio of p-nitrochlorobenzene to o-nitrochlorobenzene could reach up to 20.3. Furthermore, the selectivity distribution of nitration products was reasonably explained by the density functional theory (DFT) calculation. Finally, the possible nitration reaction pathway of chlorobenzene with NO2 was suggested in O2-Ac2O-Hβ composite catalytic system. The present work affords a new and mild nitration approach for highly selective preparation of valuable para-nitro products, and has potential industrial application prospects.
Deng, Renjie,Liu, Pingle,Luo, He'an,Ni, Wenjin,You, Kuiyi,Zhao, Fangfang
(2020/02/26)

Two-Phase Electrochemical Generation of Aryldiazonium Salts: Application in Electrogenerated Copper-Catalyzed Sandmeyer Reactions
The electrochemical generation of aryldiazonium salts from nitroarenes in a two-phase system (ethyl acetate/water) was reported for the first time. Some compounds including azo, azosulfone, and arylazides were prepared in good yields with good purity. Cathodically generated aryldiazoniums and anodically produced copper(Ι) ions were used to perform Sandmeyer reactions. To improve the method, an H-type self-driving cell equipped with a Zn rod as an anode was introduced and used for two-phase aryldiazonium production.
Goljani, Hamed,Tavakkoli, Zahra,Sadatnabi, Ali,Nematollahi, Davood
supporting information
p. 5920 - 5924
(2020/08/12)

Dehydroxyalkylative halogenation of C(aryl)-C bonds of aryl alcohols
We herein report Cu mediated side-directed dehydroxyalkylative halogenation of aryl alcohols. C(aryl)-C bonds of aryl alcohols were effectively cleaved, affording the corresponding aryl chlorides, bromides and iodides in excellent yields. Aryl alcohols could serve as both aromatic electrophilic and radical synthetic equivalents during the reaction.
Liu, Mingyang,Zhang, Zhanrong,Liu, Huizhen,Wu, Tianbin,Han, Buxing
supporting information
p. 7120 - 7123
(2020/07/14)

NITRATION
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; 66

(2020/05/28)

Metal- and base-free synthesis of aryl bromides from arylhydrazines
An efficient method was developed to synthesize brominated aromatic compounds from arylhydrazine hydrochlorides by using BBr3 in DMSO/CPME (cyclopentyl methyl ether) under air at 80 °C for 1 h without the use of bases or metal catalysts. In particular, this method could be carried out satisfactorily using electron-withdrawing groups to afford aryl bromides in a moderate to excellent yields.
Phuc Tran, Dat,Nomoto, Akihiro,Mita, Soichiro,Dong, Chun-ping,Kodama, Shintaro,Mizuno, Takumi,Ogawa, Akiya
supporting information

(2020/05/08)

Oxidative bromination of non-activated aromatic compounds with AlBr3/KNO3 mixture
Bromination of non-activated aromatic compounds with reaction mixture containing KNO3 and AlBr3 was studied in liquid substrates and in solvent. Aluminium bromide has three different roles in this reaction mixture. First, it is a source of bromide ions, which are essential in oxidative bromination application. Second, it acts as a catalyst, and lastly, it forms acidic environment via its hydrolysis, which is necessary for enhancement of the oxidising properties of nitrate ions. It was shown that when changing the reaction conditions, different side reactions (like nitration or Friedel–Crafts type arylation) can occur. However, it is possible to guide the reaction path and receive the desired outcome by choosing the suitable reaction conditions. In addition, it was shown that there has to be water content in this reaction mixture as the bromine formation rate depends on it, while there exists an optimal volume of water, where bromine formation is the fastest.
Rahu, Ida,J?rv, Jaak
p. 1219 - 1227
(2019/11/13)

Preparation method of substituted nitrobenzene compound
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 0054-0057

(2019/03/29)

The invention relates to a core of the benzimidazole and hafnium nitride compound and its application on the OLED device (by machine translation)
The invention discloses a benzimidazole and ketone compound and its in the organic electroluminescent device of the application, this compound in order to benzimidazole and ons core, has not crystallized easily between the molecules, difficult to gather, with good film forming property characteristics. The compound of the invention as OLED light-emitting device of the luminescent layer body material when in use, the current efficiency of the device, power efficiency and external quantum efficiency is greatly improved; at the same time, to improve the service life of the device is very obvious. (by machine translation)
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Paragraph 0044; 0052; 0053; 0054

(2019/05/16)

ipso-Bromination/iodination of arylboronic acids: Poly(4-vinylpyridine)-Br2/I2 complexes as safe and efficient reagents
Poly(4-vinyl pyridine) supported bromine/iodine complexes were prepared and probed for ipso-bromination/iodination of arylboronic acids. These solid complexes with catalytic amount of additive are found to be safe and efficient reagent system for the ipso-bromination/iodination. The reaction occurs under mild conditions and tolerates various functional groups resulting in products with high selectivity and yields.
Fu, Fang,Gurung, Laxman,Czaun, Miklos,Mathew, Thomas,Prakash, G.K. Surya
supporting information

(2019/08/26)

Inexpensive NaX (X = I, Br, Cl) as a halogen donor in the practical Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids under aerobic conditions
Versatile and practical Ag/Cu-mediated decarboxylative halogenation between readily available aryl carboxylic acids and abundant NaX (X = I, Br, Cl) has been achieved under aerobic conditions in moderate to good yields. The halodecarboxylation is shown to be an effective strategy for S-containing heteroaromatic carboxylic acid and benzoic acids with nitro, chloro and methoxyl substituents at the ortho position. A gram-scale reaction and a three-step procedure to synthesize iniparib have been performed to evaluate the practicality of this protocol. A preliminary mechanistic investigation indicates that Cu plays a vital role and a radical pathway is involved in the transformation.
Fu, Zhengjiang,Jiang, Ligao,Zuo, Qianming,Li, Zhaojie,Liu, Yanzhu,Wei, Zhenhong,Cai, Hu
supporting information
p. 5416 - 5421
(2018/08/12)

HNO3/HFIP: A Nitrating System for Arenes with Direct Observation of π-Complex Intermediates
This report describes an efficient nitrating system for the nitration of arenes at room temperature by using an equivalent of nitric acid in HFIP (1,1,1,3,3,3-hexafluoroisopropanol). The π-complex intermediate of an arene with a nitronium ion stabilized by HFIP can be directly observed by UV-vis spectra and is supported by theoretical calculations.
Lu, Le,Liu, Huixin,Hua, Ruimao
supporting information
p. 3197 - 3201
(2018/06/11)

Compound taking cyanobenzene as core, and application of compound in organic light-emitting devices (OLEDs)
The invention discloses a compound taking cyanobenzene as a core, and application of the compound in organic light-emitting devices (OLEDs). The compound takes the cyanobenzene as the core and takes carbazole ring groups as branch chains. The compound is characterized in that molecules do not easily crystallize and aggregate, and the compound has a good film-forming property. The compound providedby the invention can be applied to the OLEDs as a luminous layer material; the OLEDs applying the compound have good photoelectric performance and can better adapt to and meet the application requirements of panel manufacturing enterprises.
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Paragraph 0052; 0054; 0055

(2018/03/26)

A general electrochemical strategy for the Sandmeyer reaction
Herein we report a general electrochemical strategy for the Sandmeyer reaction. Using electricity as the driving force, this protocol employs a simple and inexpensive halogen source, such as NBS, CBrCl3, CH2I2, CCl4, LiCl and NaBr for the halogenation of aryl diazonium salts. In addition, we found that these electrochemical reactions could be performed using anilines as the starting material in a one-pot fashion. Furthermore, the practicality of this process was demonstrated in the multigram scale synthesis of aryl halides using highly inexpensive graphite as the electrode. A series of detailed mechanism studies have been performed, including radical clock and radical scavenger study, cyclic voltammetry analysis and in situ electron paramagnetic resonance (EPR) analysis.
Liu, Qianyi,Sun, Beiqi,Liu, Zheng,Kao, Yi,Dong, Bo-Wei,Jiang, Shang-Da,Li, Feng,Liu, Guoquan,Yang, Yang,Mo, Fanyang
p. 8731 - 8737
(2018/12/10)

PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES
The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.
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Paragraph 00138

(2017/07/28)

PROCESS FOR THE PREPARATION OF ORGANIC HALIDES
The present invention provides a halo-de-carboxylation process for the preparation of organic chlorides, organic bromides and mixtures thereof, from their corresponding carboxylic acids, using a chlorinating agent selected from trichloroisocyanuric acid (TCCA), dichloroisocyanuric acid (DCCA), or combination thereof, and a brominating agent.
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Paragraph 00120; 00121; 00122

(2017/08/01)

Synthetic method of aryl halide taking aryl carboxylic acid as raw material
A synthetic method of an aryl halide taking aryl carboxylic acid as a raw material is characterized in that a corresponding aryl halide is formed by carrying out substitution reaction on an aryl carboxylic acid compound and haloid salt MX in an organic solvent under the condition that oxygen, a silver catalyst, a copper additive and a bidentate nitrogen ligand exist, wherein M in MX represents alkali metal or alkaline earth metal, and X represents F, Cl, Br or I. Compared with a conventional aryl halide synthetic method, the synthetic method disclosed by the invention has the obvious advantages that reaction raw materials (comprising aryl carboxylic acid and MX) are cheap and easy to obtain, the using amount of a metal catalyst is small, pollution to the environment when the oxygen is used as an oxidant is the smallest, good tolerance to various functional groups on an aromatic ring is obtained, the yield is high, and the like. The synthetic method disclosed by the invention can be widely applied to synthesis in the fields of medicine, materials, natural products and the like in industry and academia.
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Paragraph 0091

(2018/01/03)

NH4I/tert-butyl hydroperoxide-promoted oxidative C–N cleavage of tertiary amines leading to nitroaromatic compounds
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
p. 504 - 508
(2017/10/03)

Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions
Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.
Fu, Zhengjiang,Li, Zhaojie,Song, Yuanyuan,Yang, Ruchun,Liu, Yanzhu,Cai, Hu
p. 2794 - 2803
(2016/04/26)

Regioselective mononitration of aromatic compounds with N2O5 by acidic ionic liquids via continuous flow microreactor
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
p. 513 - 516
(2016/01/20)

NITRATION OF AROMATIC COMPOUNDS
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.
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Paragraph 0052

(2016/08/17)

Transition-metal-free synthesis of thiocyanato- or nitro-arenes through diaryliodonium salts
A transition-metal-free approach to facile synthesis of thiocyanato- and nitro-arenes was developed from KSCN (potassiumthiocyanate) or NaNO2with diaryliodonium salts in good yields under mild conditions. The reaction was compatible with a variety of sensitive functional substituents such as halides and nitro and ester groups. The usefulness of arylation products has been realized. (Formula Present).
Li, Xiao-Hua,Li, Liang-Gui,Mo, Xue-Ling,Mo, Dong-Liang
supporting information
p. 963 - 970
(2016/07/07)

Poly(4-vinylpyridine)-nitrating mixture complex (PVP-NM): Solid nitrating mixture equivalent for safe and efficient aromatic nitration
Friedel-Crafts type aromatic nitration has served as an indispensable reaction within both industrial and academic applications. However, growing concern over the use of copious amounts of strong acids has prompted the search for more environmentally friendly alternatives. Polymer-bound Bronsted acids, on the other hand, have been shown useful as convenient alternatives to liquid acids. Nitric acid and sulfuric acids have, therefore, been combined, both individually and as a mixture, with poly(4-vinylpyridine). The new solid acid systems have been used to nitrate both activated and deactivated arenes under mild conditions and proved to be effective nitrating agent.
Surya Prakash,Gurung, Laxman,Glinton, Kevin E.,Belligund, Kavita,Mathew, Thomas,Olah, George A.
supporting information
p. 3446 - 3451
(2015/06/25)

Bismuth triflate catalyzed mononitration of aromatic compounds with N 2O5
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
p. 509 - 512
(2014/05/20)

Phosphoric acid modified montmorillonite clay: A new heterogeneous catalyst for nitration of arenes
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.
p. 124 - 128
(2014/12/11)

Oxidation of aromatic amines into nitroarenes with m-CPBA
A versatile and highly efficient approach for the synthesis of nitroarenes from aromatic amine using m-CPBA has been developed. This oxidation reaction was operationally straightforward and proceeded to afford products in good isolated yields.
Liu, Jia,Li, Jue,Ren, Jiangmeng,Zeng, Bu-Bing
p. 1581 - 1584
(2014/03/21)

Click chemistry inspired facile synthesis and bioevaluation of novel triazolyl analogs of Ludartin
A convenient and modular synthesis involving diastereoselective Michael addition followed by regioselective Huisgen 1,3-dipolar cycloaddition reaction was carried out to furnish 1,4-disubstituted-1,2,3-triazoles of Ludartin. This reaction scheme involving Michael addition followed by regioselective Huisgen 1,3-dipolar cycloaddition reaction leading to the formation of triazolyl analogs is being reported for the first time. All the triazolyl products were characterised using spectral data analysis. Sulphorhodamine B cytotoxicity screening of the resulting products against a panel of five human cancerous cell-lines revealed that few of the analogs display promising broad spectrum cytotoxic effect. Among all the synthesized compounds, only 3q displayed the best cytotoxic effect with IC50 values of 12, 11, 38, 39 and 8.5 μM but less than the standard Ludartin (1) with IC50 values of 6.3, 7.4, 7.5, 6.9 and 0.5 μM against human neuroblastoma (T98G), lung (A-549), prostate (PC-3), colon (HCT-116) and breast (MCF-7) cancer cell lines, respectively. The present synthesis was designed based on the previous literature reports of Ludartin as an aromatase inhibitor. Our work provides an initial study on structure-activity relationship of triazolyl analogs of sesquiterpene lactones in general and Ludartin (1) in particular.
Lone, Shabir H.,Bhat, Khursheed A.,Majeed, Rabiya,Hamid, Abid,Khuroo, Mohd A.
p. 1047 - 1051
(2014/03/21)

2-Aryl-3H-indol-3-ones: Synthesis, electrochemical behaviour and antiplasmodial activities
The synthesis of indolone derivatives and their antiplasmodial activity in vitro against Plasmodium falciparum at the blood stage are described. The 2-aryl-3H-indol-3-ones were synthesized via deoxygenation of indolone-N-oxides. Electrochemical behaviour, antiplasmodial activity and cytotoxicity on human tumor cell lines were compared to those of indolone-N-oxides. The antiplasmodial IC50 (concentrations at 50% inhibition) of these compounds ranged between 49 and 1327 nM. Among them, the 2-(4-dimethylaminophenyl)-5-methoxy- indol-3-one, 7, had the best antiplasmodial activity in vitro (IC50 = 49 nM; FcB1 strain) and selectivity index (SI (CC50 MCF7/IC 50 FcB1) = 423.4). Thus, the hits identified in this deoxygenated series correspond to their structural homologs in the N-oxide series with comparable electrochemical behaviour at the nitrogen-carbon double bond.
Najahi, Ennaji,Valentin, Alexis,Fabre, Paul-Louis,Reybier, Karine,Nepveu, Fran?oise
p. 269 - 274
(2014/04/17)

Halogenation and DNA cleavage via thermally stable arenediazonium camphorsulfonate salts
A series of stable arenediazonium camphorsulfonate salts (2a-2j) were synthesized by simple diazotization of several aromatic amines in the presence of sodium nitrite and camphorsulfonic acid. All the new arenediazonium camphorsulfonates, which were characterized by multinuclear (1H and 13C) NMR, IR, DSC, and X-ray diffraction analysis (2e and 2f) provide unambiguous proof for the molecular structures of 2e and 2f. The efficient application of these salts in halogenation reactions was studied in solvent and solvent-free conditions and the DNA cleavage activity was also assessed. These arenediazonium camphorsulfonate salts are noticed as efficient DNA cleaving agents.
Vajpayee, Vaishali,Moon, Mi Eun,Lee, Sunmi,Ravikumar, Sambandam,Kim, Hyunuk,Ahn, Byungchan,Choi, Seoyoon,Hong, Soon Ho,Chi, Ki-Whan
p. 3511 - 3517
(2013/04/23)

Preparation of heteropoly acid based amphiphilic salts supported by nano oxides and their catalytic performance in the nitration of aromatics
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
p. 2197 - 2202
(2013/03/14)

Regioselective nitration of aromatics with nanomagnetic solid superacid SO42-/ZrO2-MxOy-Fe 3O4 and its theoretical studies
A series of micro- and nanosulfated zirconia loaded on Fe3O 4 or other metal oxides (SO42-/ZrO 2-MxOy-Fe3O4 (M=Ti 4+, V5+, and Zn2+)) was prepared, characterized, and used in nitration. The nitration conditions with these solid superacids were then optimized to achieve the best regioselectivity and improve the performances of the catalysts as well. In the experimental results, SZTF (SO42-/ZrO2-TiO2-Fe 3O4) showed excellent catalytic activity and it increased the surface area of SO42-/ZrO2 by up to 15 %. The increase not only facilitated the generation of NO2+, but also provided more opportunities for metal ions to interact with aromatic compounds. With chlorobenzene as substrate, theoretical research on its geometric parameters, electron clouds, and electron spin density was used to investigate the interaction between transition metals and chlorobenzene.
Wang, Peng Cheng,Zhu, Jie,Liu, Xiang,Lu, Ting Ting,Lu, Ming
p. 310 - 317
(2013/08/23)

Efficient ipso-nitration of arylboronic acids with iron nitrate as the nitro source
A novel, simple and efficient ipso-nitration of arylboronic acids with iron nitrate has been developed. The protocol uses readily available arylboronic acids as the starting materials, inexpensive iron nitrate (0.5 equiv.) as the nitro source without addition of an additive, and the corresponding nitroarenes were obtained in good to excellent yields.
Jiang, Min,Yang, Haijun,Li, Yong,Jia, Zhiying,Fu, Hua
p. 25602 - 25604
(2013/12/04)

Synthesis and biological evaluation of new bis-indolone-N-oxides
A series of bis-indolone-N-oxides, 1a-f, was prepared from bis(ethynyl)benzenes and o-halonitroaryls and studied for their in vitro antiplasmodial activities against Plasmodium falciparum and representative strains of bacteria and candida as well as for their cytotoxicity against a human tumor cell line (MCF7). They did not cause any haemolysis (300 μg mL-1). Of the synthesized bis-indolones, compound 1a had the most potent antiplasmodial activity (IC50 = 0.763 μmol L-1 on the FcB1 strain) with a selectivity index (CC50 MCF7/IC 50 FcB1) of 35.6. No potency against the tested microbial strains was observed.
Najahi, Ennaji,Valentin, Alexis,Tene, Nathan,Treilhou, Michel,Nepveu, Francoise
p. 16 - 21
(2013/07/27)

Rare earth metal triflates catalyzed electrophilic nitration using N 2O5
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
experimental part
p. 73 - 76
(2012/03/26)

Selective nitration of aromatic compounds catalyzed by Hβ zeolite using N2O5
A selective and efficient process for the electrophilic nitration is described using N2O5 as a green nitrating agent, Hβ zeolite as a solid acid catalyst and shape controlling agent under mild conditions.
Ma, Xiao Ming,Li, Bin Dong,Chen, Lei,Lu, Ming,Lv, Chun Xu
scheme or table
p. 809 - 812
(2012/08/08)

Aromatic nitration with bismuth nitrate in ionic liquids and in molecular solvents: A comparative study of Bi(NO3)3·5H 2O/[bmim][PF6] and Bi(NO3)3· 5H2O/1,2-DCE systems
A suspension of bismuth nitrate pentahydrate (BN) in [bmim][PF6] or [bmim][BF4] imidazolium ionic liquid (IL) is an effective reagent for ring nitration of activated aromatics under mild conditions without the need for external promoters. Nitration can also be effected in 1,2-DCE, MeCN, or MeNO2 without additives. Nitration of activated arenes (anisole, toluene, ethylbenzene, cumene, p-xylene, mesitylene, durene, and 1,3-dimethoxybenzene) is considerably faster (time to completion) in BN/[bmim][PF6] relative to BN/1,2-DCE and there are also differences in isomer distributions (for anisole, toluene, and ethylbenzene). With introduction of strongly deactivating substituents (-CHO; -MeCO; -NO 2) the BN/IL system is no longer active but reactions still proceed with BN/1,2-DCE in reasonable yields. The ready availability and low cost of BN, simple operation, and absence of promoters, coupled to recycling and reuse of the IL, provide an attractive alternative to classical nitration methods for activated arenes. Switching from Bi(NO3)3·5H 2O/[bmim][PF6] to Bi(NO3)3· 5H2O/1,2-DCE increases the scope of the substrates that can be nitrated.
Jacoway, Jonathan,Kumar, G. G. K. S. Narayana,Laali, Kenneth K.
p. 6782 - 6785,4
(2012/12/12)

Reusable and efficient polystryrene-supported acidic ionic liquid catalyst for mononitration of aromatic compounds
A series of polystyrene-supported 1-(propyl-3-sulfonate)-3-methyl- imidazolium hydrosulfate acidic ionic liquid (PS-[SO3H-PMIM][HSO 4]) catalysts were prepared and tested for mononitration of simple aromatics compounds with nitric acid. It was found that the reactivity of the catalysts increased with increasing [SO3HPMIM][ HSO4] content. The para-selectivity was not only related to the [SO 3H-PMIM][HSO4] content but also the substituent groups in aromatics. A reaction mechanism of nitration over this new catalyst was proposed. The catalytic activity of this catalyst decreased slightly after fifth runs in the synthesis of nitrotoluene.
Li, Li Xia,Ling, Qi Long,Liu, Zu Liang,Xing, Xiao Dong,Zhu, Xiao Qin,Meng, Xiao
p. 3373 - 3377
(2013/01/15)

Protodecarboxylation of benzoic acids under radical conditions
A new approach to protodecarboxylation is described that enhances the substrate scope for benzoic acids. The reaction uses oxidative radical conditions to decarboxylate a variety of acids in acetonitrile.
Seo, Sangwon,Taylor, John B.,Greaney, Michael F.
supporting information; experimental part
p. 8270 - 8272
(2012/09/07)

A novel mode of reactivity for gold(I): The decarboxylative activation of (hetero)aromatic carboxylic acids
Gold(I) salts are found to mediate the decarboxylation of a variety of aromatic and heteroaromatic carboxylic acids at significatively lower temperatures (as low as 60°C) than the currently used copper(I) (180-190°C) and silver(I) (80-140°C) systems. In contrast to silver(I)- and copper(I)-mediated decarboxylations, the resulting aryl-gold(I) complexes are stable towards protodemetallation and can be readily isolated.
Cornella, Josep,Rosillo-Lopez, Martin,Larrosa, Igor
supporting information; experimental part
p. 1359 - 1366
(2011/06/26)

Regioselectivity nitration of aromatics with N2O5 in PEG-based dicationic ionic liquid
Regioselective mononitration of simple aromatic compounds has been investigated with N2O5 as nitrating agent and a new PEG200-based dicationic acidic ionic liquid (PEG200-DAIL) as catalyst. The results of experiments show that this nitration system can significantly improve the para-selectivity of alkyl-benzenes and the ortho-selectivity of halogenated-benzenes. The PEG200-DAIL exhibits recyclable temperature-dependant phase behavior in CCl4 solvent, and it can be recycled without apparent loss of catalytic activity, and only 5% loss of weight is observed after six times recycling.
Wang, Peng-Cheng,Lu, Ming
supporting information; experimental part
p. 1452 - 1455
(2011/05/16)

An efficient and eco-friendly MoO3-SiO2 solid acid catalyst for electrophilic aromatic nitration with N2O5
Electrophilic aromatic nitration using N2O5 as a green nitrating agent catalyzed by MoO3-SiO2 under mild conditions has been described. A series of MoO3-SiO2 catalysts with varying MoO3 loadings (5-20 mol%) were prepared by sol-gel technique and characterized using FTIR, XRD, SEM, BET and NH 3-TPD to study its surface properties. MoO3-SiO 2 shows good catalytic activity and reusability for the nitration of alkyl and halogen aromatics giving high conversions, but less efficiency for the deactivated aromatics. Reactions conducted under non-acidic conditions using N2O5 makes the process safe and environmentally friendly. Graphical Abstract: [Figure not available: see fulltext.]
Ma, Xiaoming,Li, Bindong,Lv, Chunxu,Lu, Ming,Wu, Jian,Liang, Linjie
experimental part
p. 1814 - 1820
(2012/03/08)

General copper-catalyzed transformations of functional groups from arylboronic acids in water
A simple and general copper-catalyzed method has been developed for transformations of various functional groups (i I, i N3, i SO2R, i OH, i NH2, and i NO 2) on aromatic rings from arylboronic acids in water under air. The protocol uses cheap and readily available inorganic salts (KI, NaN3, NaSO2R, NaOH, NaNO2) and aqueous ammonia as the functional-group sources, simple Cu2O/NH3 as the catalyst system, environmentally friendly water as the solvent, and oxygen in air as the oxidant. Importantly, the copper catalyst system in water was recyclable. This study should provide a useful strategy for interconversions of the functional groups on aromatic rings.
Yang, Haijun,Li, Yong,Jiang, Min,Wang, Junmei,Fu, Hua
experimental part
p. 5652 - 5660
(2011/06/23)

Silver-catalyzed decarboxylative halogenation of carboxylic acids
Decarboxylative halogenation of carboxylic acids catalyzed by silver carbonate is reported. ortho-Nitrobenzoic acids react with copper(II) chloride or bromide in DMF/DMSO at 130-140 °C leading to the corresponding aryl halides in moderate to good yields.
Luo, Yong,Pan, Xiaolin,Wu, Jie
supporting information; experimental part
p. 6646 - 6648
(2011/02/21)

Efficient and economic halogenation of aryl amines via arenediazonium tosylate salts
Arenediazonium tosylate salts have been successfully employed as a new and efficient reagent in halogenation reactions. A novel and economic protocol has been developed for the bromination and chlorination of various anilines using arenediazonium tosylate salts. A wide variety of reaction conditions were studied in acetonitrile at either room temperature or 60 °C in the presence or absence of catalyst with good to excellent yields. A surprising result showed the formation of acetanilides as a major product of aniline and methyl-substituted aniline halogenations in high yields.
Lee, Young Min,Moon, Mi Eun,Vajpayee, Vaishali,Filimonov, Victor D.,Chi, Ki-Whan
experimental part
p. 7418 - 7422
(2010/10/01)

An expeditious and environmentally benign preparation of aryl halides from aryl amines by solvent-free grinding
An efficient solvent-free methodology for conversion of various aryl amines into bromides and chlorides via arenediazonium tosylate salts under grinding conditions is disclosed. This new methodology not only avoids the use of strong acids and expensive reagents for diazotization-halogenation reactions, but also decreases the amount of organic waste from the reaction process.
Moon, Mi Eun,Choi, Younghwa,Lee, Young Min,Vajpayee, Vaishali,Trusova, Marina,Filimonov, Victor D.,Chi, Ki-Whan
scheme or table
p. 6769 - 6771
(2011/03/17)

Fast and efficient nitration of salicylic acid and some other aromatic compounds over H3PO4/TiO2-ZrO2 using nitric acid
TiO2-ZrO2 (1/1)-surf with Ti and Zr molar ratio of 1/1 was prepared with surfactant through a sol-gel method. The optimum experimental condition was investigated for nitration of salicylic acid. Then, a number of nitration reactions were carried out with a variety of aromatic compounds in the optimum condition. The 25 wt% H3PO4/TiO2-ZrO2 (1/1)-surf catalyst showed good selectivity and yield in a short time for the nitration of salicylic acid and some other aromatic compounds.
Kalbasi, Roozbeh Javad,Massah, Ahmad Reza,Zamani, Farzad,Hamid, Javaherian Naghash
experimental part
p. 397 - 403
(2010/10/20)

Nitration of aromatic hydrocarbons and halobenzenes using NOx catalyzed by solid acid catalysts
The nitration of aromatics using zeolite as a solid inorganic catalyst and nitric oxides as nitrating agents is a relatively clean process for aromatic nitration. Copyright
Pande, Manoj A.,Samant, Shriniwas D.
experimental part
p. 3734 - 3738
(2011/02/16)

Synthesis and antiplasmodial activity of new indolone N-Oxide derivatives
A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), aswell as for cytotoxic concentration (CC50) on MCF7 and KB human tumor cell lines. Compound 26 (5-methoxy-indolone-N-oxide analogue) had the most potent antiplasmodial activity in vitro (50 MCF7/IC50 FcB1: 14623; CC50 KB/IC50 3D7: 198823). In in vivo experiments, compound 1 (dioxymethylene derivatives of the indolone-N-oxide) showed the best antiplasmodial activity against Plasmodium berghei, 62% inhibition of the parasitaemia at 30 mg/kg/day. 2009 American Chemical Society.
Nepveu, Fran?oise,Kim, Sothea,Boyer, Jeremie,Chatriant, Olivier,Ibrahim, Hany,Reybier, Karine,Monje, Marie-Carmen,Chevalley, Severine,Perio, Pierre,Lajoie, Barbora H.,Bouajila, Jalloul,Deharo, Eric,Sauvain, Michel,Tahar, Rachida,Basco, Leonardo,Pantaleo, Antonella,Turini, Francesco,Arese, Paolo,Valentin, Alexis,Thompson, Eloise,Vivas, Livia,Petit, Serge,Nallet, Jean-Pierre
experimental part
p. 699 - 714
(2010/07/09)

Lanthanide Bis[(trifluoromethyl)sulfonyl]imides as reusable catalysts for mononitration of substituted benzenes in ionic liquids
Lanthanide bis[(trifluoromethyl)sulfonyl]imides as a kind of effective catalyst were used in quaternary ammonium ionic liquids to afford a useful new method for the nitration of substituted benzenes with concentrated nitric acid (95%) as nitrating agent. The less expensive lanthanum bis[(trifluoromethyl) sulfonyl]imide was found to be the most effective catalyst employed in the ionic liquid tributylammonium bis[(trifluoromethyl)sulfonyl]imide. The lanthanum bis[(trifluoromethyl)sulfonyl]-imide/tributylammonium bis[(trifluoromethyl) sulfonyl]imide system demonstrated high catalytic activity for the nitration of halobenzenes and rendered good to excellent yields. This catalyst/ionic liquid system could be recovered by simple procedures and recycled for at least 5 times.
Wang, Shuojin,Jiang, Shaojie,Nie, Jin
experimental part
p. 1939 - 1945
(2011/02/28)