- Pronounced catalytic effect of micellar solution of sodium dodecyl sulfate (SDS) for regioselective iodination of aromatic compounds with a sodium iodide/cerium(IV) trihydroxide hydroperoxide system
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Micellar solutions of sodium dodecyl sulfate (SDS) catalyze the regioselective iodination of a wide range of aromatic compounds with sodium iodide in the presence of the easily prepared, water-resistant and recyclable cerium(IV) trihydroxide hydroperoxide, Ce(OH)3O2H, at room temperature. By this protocol, structurally diverse aromatic compounds including benzene and naphthalene were iodinated in good to excellent yields.
- Firouzabadi, Habib,Iranpoor, Nasser,Garzan, Atefeh
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Read Online
- A simple and efficient iodination of aromatic compounds using I2/Choline Chloride/K2S2O8
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A simple and efficient method for the iodination of aromatic compounds has been achieved in the presence of molecular iodine, choline chloride and potassium peroxodisulfate at 65 °C in acetonitrile. The rate of conversion of aromatic compounds into iodoaromatic compounds was promoted by in situ formed choline peroxodisulfate. This protocol provides an efficient access to iodoarenes with operational simplicity, good functional group tolerance and a moderate to good product yield.
- Parthiban,Joel Karunakaran
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Read Online
- PURIFIED CRYSTALLINE DETOMIDINE HYDROCHLORIDE MONOHYDRATE, ANHYDRATE AND FREE BASE WITH LOW AMOUNTS OF ISO-DETOMIDINE AND OTHER IMPURITIES BY RECRYSTALLISATION IN WATER
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The present disclosure relates to crystalline detomidine hydrochloride monohydrate, anhydrous detomidine hydrochloride and detomidine free base (4-[(2,3-dimethylphenyl)methyl]-1H-lmidazole ), purified by recrystallisation in water, with a low amount (total amount of impurities is not more than 0.1% area relative to detomidine based on HPLC, UV detection at 220 nm) of the impurities iso-detomidine (4-[(3,4-dimethylphenyl)methyl]-1H-lmidazole ), iso-impurity A (((RS)-(3,4-dimethylphenyl)(1H-imidazol-4-yl)methanol)), impurity A ((RS)-(2,3-dimethylphenyl)(1H-imidazol-4-yl)methanol), "ketone impurity" (2,3-dimethylphenyl)(1H-imidazol-4-yl) methanone, impurity B ((RS)-(1-benzyl-1H-imidazol-5-yl)(2, 3-dimethyl phenyl) methanol) and impurity C (4-[(2,3-dimethylcyclohexyl)methyl]-1H-imidazole). Also disclosed are processes for recrystallising detomidine hydrochloride monohydrate from commercially available anhydrous detomidine hydrochloride in water, pharmaceutical compositions comprising detomidine hydrochloride in purified form for use as an analgesic in methods of treating human subjects, a process for validating a batch of detomidine hydrochloride drug substance by determining the content of impurities iso-detomidine and iso- impurity A by HPLC, as well as XRPD, DSC and TGA data of crystalline detomidine free base.
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Page/Page column 26; 27
(2020/02/14)
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- Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds
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Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.
- Iida, Keisuke,Ishida, Shunsuke,Watanabe, Takamichi,Arai, Takayoshi
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- Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds
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Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.
- Iida, Keisuke,Ishida, Shunsuke,Watanabe, Takamichi,Arai, Takayoshi
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p. 7411 - 7417
(2019/06/18)
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- N-Iodosuccinimide (NIS) in Direct Aromatic Iodination
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N-Iodosuccinimide (NIS) in pure trifluoroacetic acid (TFA) offers a time-efficient and general method for the iodination of a wide range of mono- and disubstituted benzenes at room temperature, as demonstrated in this paper. The starting materials were generally converted into mono-iodinated products in less than 16 hours at room temperature, without byproducts. A few deactivated substrates needed addition of sulfuric acid to increase the reaction rate. Another exception was methoxybenzenes that preferentially were iodinated by NIS in acetonitrile with only catalytic amounts of TFA.
- Bergstr?m, Maria,Suresh, Ganji,Naidu, Veluru Ramesh,Unelius, C. Rikard
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p. 3234 - 3239
(2017/06/21)
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- Easy Access to Difluoromethylene-Containing Arene Analogues through Palladium-Catalysed C–H Olefination
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An efficient palladium-catalysed ortho-C–H olefination of α,α-difluorophenylacetic acid derivatives using 8-aminoquinoline as a bidentate directing group has been developed. A range of olefinated arenes can thus be synthesized in a concise way. This reaction provides an easy and straightforward route to a panel of difluoromethylated arene analogues in moderate to good yields, with a satisfactory tolerance of common functional groups. Transformation of the products into a variety of other difluoromethylene-containing compounds demonstrates the utility of this method.
- Shao, Changdong,Shi, Guangfa,Zhang, Yanghui
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supporting information
p. 5529 - 5538
(2016/11/25)
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- Synthesis of polysubstituted iodobenzene derivatives from alkynylsilanes and 1,3-dienes via diels-alder/oxidation/iodination reaction sequence
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The cobalt-catalyzed Diels-Alder reaction of trimethylsilyl-substituted alkynes with 1,3-dienes led to dihydroaromatic intermediates which were transformed into iodobenzene derivatives. For this transformation, the dihydroaromatic intermediates had to be oxidized and the trimethylsilyl-substituted arene had to undergo a silicon-iodine exchange reaction. For this purpose, a number of oxidizing agents and iodonium sources were tested in order to realize the desired two transformations in a single step. Eventually, the combination of tert-butyl hydroperoxide (TBHP), zinc iodide, and potassium carbonate led to the desired oxidation/iodination in good to excellent yields in a short reaction time at ambient temperatures.
- Mockel, Robert,Hilt, Gerhard
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supporting information
p. 1644 - 1647
(2015/04/14)
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- Efficient and direct iodination of alkyl benzenes using polymer/HIO4 and I2 under mild condition
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An efficient and rapid method has been found for the iodination of aromatic compounds using iodine and polymer-supported periodic acid (PSPIA) as an oxidant under mild aprotic conditions. The reagent after the completion of the reaction was easily removed by filtration and was regenerated for further use. This method has some advantages such as: mild reaction conditions, straight forward procedure, inexpensive method, high yields and one-pot conversion.
- Bahrami-Nasab, Sepideh,Nazifi, S. Mohamad Reza,Pourali, Ali Reza
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p. 305 - 308
(2014/06/24)
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- Mild and selective organocatalytic iodination of activated aromatic compounds
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We describe an organocatalytic iodination of activated aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) as the iodine source with thiourea catalysts in acetonitrile. The protocol is applicable to a number of aromatic substrates with significantly different steric and electronic properties. The iodination is generally highly regioselective and provides high yields of isolated products. NMR kinetic investigations conducted in THF-d 8indicate the role of sulfur in the thiourea motif as a nucleophile that is assisted by H-bonding in the key steps of the reaction. Georg Thieme Verlag Stuttgart . New York.
- Jakab, Gergely,Hosseini, Abolfazl,Hausmann, Heike,Schreiner, Peter R.
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supporting information
p. 1635 - 1640
(2013/07/27)
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- Aromatic iodination using N-iodosaccharin in room temperature ionic liquids
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More reactive iodination conditions have been developed that combine the use of room temperature ionic liquids with N-iodosaccharin. Using these reaction conditions, even very modestly activated arenes such as toluene can be iodinated in good yield under very mild conditions.
- Bailey, Lindsey,Handy, Scott T.
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experimental part
p. 2413 - 2414
(2011/05/09)
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- METHOD OF PRODUCING IODIZING AGENT, AND METHOD OF PRODUCING AROMATIC IODINE COMPOUND
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A method of the present invention, for producing an iodizing agent, includes the step of electrolyzing iodine molecules in a solution by using an acid as a supporting electrolyte. This realizes (i) a method of producing an iodine cation suitable for use as an iodizing agent that does not require a sophisticated separation operation after iodizing reaction is completed, and (ii) an electrolyte used in the method. Further, a method of the present invention, for producing an aromatic iodine compound, includes the step of causing an iodizing agent, and an aromatic compound whose nucleus has one or more substituent groups and two or more hydrogen atoms, to react with each other under the presence of a certain ether compound. This realizes such a method of producing an aromatic iodine compound that position selectivity in iodizing reaction of an aromatic compound is improved.
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(2010/05/13)
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- S1P RECEPTORS MODULATORS
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The invention relates to novel compounds that have S1P receptor modulating activity and, preferably, apoptotic activity and/or anti proliferative activity against cancer cells and other cell types. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, cancer. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as cancer.
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Page/Page column 45
(2010/04/30)
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- Iodination of activated aromatic compounds using sodium peroxodisulfate and iodine: An efficient way to iodinate alkylated calix[4]arenes
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A simple method for the iodination of activated arenes, using molecular iodine and sodium peroxodisulfate as the oxidant, is presented. The reaction is conducted in the presence of catalytic amounts of tetramethylammonium iodide as a phase-transfer catalyst in acetonitrile. For non-polar substances, which are not soluble in pure acetonitrile such as calix[4]arenes bearing long alkyl chains, a modified reaction is introduced. In this case the phase-transfer catalyst is changed to methyltriphenylphosphonium peroxodisulfate. Chloroform as a cosolvent mediates solubility. Furthermore, we show that the slightly basic conditions obtained upon the addition of sodium bicarbonate have a beneficial effect on the yield. Georg Thieme Verlag Stuttgart.
- Barton, Olaf G.,Mattay, Jochen
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p. 110 - 114
(2008/09/20)
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- Practical electrochemical iodination of aromatic compounds
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A practical method for electrochemical iodination of aromatic compounds was developed. The method involves the generation of I+ by electrochemical oxidation of I2 in CH3CN using H 2SO4 as supporting electrolyte followed by the reaction with aromatic compounds. The para/ortho selectivity for the reaction of mono-substituted benzenes was significantly improved using dimethoxyethane as cosolvent in the second step. The reaction with highly reactive aromatic compounds led to the formation of significant amounts of diiodo compounds in a macrobatch reactor. This problem was solved by fast 1:1 mixing of I+ with an aromatic compound using a microflow system consisting of a T-shaped micromixer and a microtube reactor.
- Kataoka, Kazuhide,Hagiwara, Yuji,Midorikawa, Koji,Suga, Seiji,Yoshida, Jun-Ichi
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p. 1130 - 1136
(2013/01/03)
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- Grindstone chemistry: (Diacetoxyiodo)benzene-mediated oxidative nuclear halogenation of arenes using NaCl, NaBr or I2
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A technique of "Grindstone chemistry" is applied to the solvent-free halogenation of arenes with NaCl, NaBr or I2 using (diacetoxyiodo)benzene as the oxidant. Improved yields and higher purities of the products are observed compared with those from established methods.
- Karade,Tiwari,Huple,Siddiqui
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p. 366 - 368
(2007/10/03)
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- HIO4/Al2O3 as a new system for iodination of activated aromatics and 1,3-dicarbonyl compounds
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The use of a periodic acid/alumina system for the iodination of activated aromatics and 1,3-dicarbonyl compounds is described.
- Khalilzadeh, Mohammad A.,Hosseini, Abolfazl,Shokrollahzadeh, Mojtaba,Halvagar, Mohammad R.,Ahmadi, Daryoush,Mohannazadeh, Farajollah,Tajbakhsh, Mahmoud
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p. 3525 - 3528
(2007/10/03)
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- PROCESS FOR PRODUCTION OF IODINE COMPOUNDS AND PROCESS FOR PRODUCTION OF HIGH-PURITY 5-IODO-2-METHYLBENZOIC ACID
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Provided is a production method for an iodine compound in which iodine is reacted with a substrate in the presence of a porous material having a pore diameter of 500 nm or less or in the presence of the above porous material and an oxidizing agent and a production process for high purity 5-iodo-2-methylbenzoic acid comprising an iodination reaction step carried out by the above-mentioned, a crystal precipitation and separation step in which a product is precipitated by adding water or cooling and then separated and a purification step in which crystal separated is recrystallized using an organic solvent. According to the production method for an iodine compound described above, iodine can be introduced into various substrates at a high selectivity. Since expensive metals and specific reagents do not have to be used, it can readily be carried out in an industrially scale, and the product having a high purity can be obtained. Further, the process comprising the iodination reaction, separation and purification steps described above makes it possible to readily obtain at a high yield, 5-iodo-2-methylbenzoic acid having a high purity which is useful in uses for functional chemical products such as medicines. The process of the present invention comprising iodination reaction, separation and purification steps is characterized by that it is simple in terms of a procedure and that the purification load is smaller, and it is very advantageous in industrially carrying out.
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(2008/06/13)
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- A comparison of microwave-accelerated and conventionally heated iodination reactions of some arenes and heteroarenes, using ortho-periodic acid as the oxidant
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A fast and simple method for the oxidative iodination of some activated arenes and heteroarenes, either under microwave irradiation or by conventional heating, is reported, using diiodine and ortho-periodic acid as the oxidant. The reactions were carried out in hot 95% ethanol under a reflux condenser. For the microwave assisted reactions, the reaction times were always notably shortened, but the yields were nearly the same as those afforded by the conventional method.
- Sosnowski, Maciej,Skulski, Lech
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p. 401 - 406
(2007/10/03)
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- Effective and regioselective iodination of arenes using iron(III) nitrate in the presence of tungstophosphoric acid
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An easy, cheap, and effective method for iodination of various aromatic compounds takes place with molecular iodine and iron nitrate nonahydrate as the oxidant in the presence of a catalytic amount of tungstophosphoric acid in dichloromethane, with good yield and high regioselectivity under very mild conditions.
- Jafarzadeh, Mohammad,Amani, Kamal,Nikpour, Farzad
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p. 1808 - 1811
(2007/10/03)
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- Simple and regioselective oxyiodination of aromatic compounds with ammonium iodide and Oxone
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Oxyiodination of aromatic compounds using NH4I and Oxone gives high yields and selectivity. A simple method for the iodination of aromatic compounds using NH4I as the iodine source and Oxone as the oxidant is described.
- Krishna Mohan,Narender,Kulkarni
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p. 8015 - 8018
(2007/10/03)
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- Efficient method for the preparation of aromatic bromides and iodides by ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate-catalyzed halogenation with bromine and iodine monochloride
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Direct iodination and bromination of various aromatic compounds with 1.1-2.0 molar amounts of iodine monochloride (ICl) and 1.1-3.0 molar amounts of bromine proceeded smoothly to afford the corresponding aromatic iodides and bromides, respectively, in good to excellent yields by using 0.05 molar amount of ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, Cp2FeB[3,5-(CF3)2C6H 3]4 (1), in the presence of ZnO. Iodination of toluene in the co-existence of 0.5 molar amount of DDQ also proceeded to give iodotoluenes in high yield.
- Kitagawa, Hideo,Shibata, Tsuyoshi,Matsuo, Jun-Ichi,Mukaiyama, Teruaki
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p. 339 - 345
(2007/10/03)
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- Regioselective oxyiodination of aromatic compounds using potassium iodide and oxone
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A highly efficient, simple, mild and regioselective method for oxyiodination of aromatic compounds is reported. The electrophilic substitution of iodine generated in situ from KI as an iodine source and oxone as an oxidant for the first time.
- Narender,Srinivasu,Kulkarni,Raghavan
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p. 2319 - 2324
(2007/10/03)
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- Aromatic iodination with iodine monochloride by using a catalytic amount of ferrocenium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate
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Direct iodination reaction of several aromatic compounds with 1.1-2.0 molar amounts of iodine monochloride (IC1) proceeded smoothly to afford the corresponding aromatic iodides in good to excellent yields by using 5 mol% of Cp2FeB[3,5-(CF3)2C6H3]4 (1) in the coexistence of DDQ or ZnO. (C) 2000 Published by Elsevier Science Ltd.
- Mukaiyama,Kitagawa,Matsuo
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p. 9383 - 9386
(2007/10/03)
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- Selective Oxidative Iodination of Aromatic Compounds
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Optimal conditions have been found for oxidative iodination of aromatic compounds in the system KI-H2SO4-HNO3-H2O in the presence of O2, and the kinetics and mechanism of the reaction have been studied. The process involves oxidation of I- to I+ with NO+2 ion, arene iodination with I+, and oxidation of HNO2 to HNO3 with oxygen.
- Dorfman,Aleshkova
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p. 1585 - 1597
(2007/10/03)
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- An efficient and regioselective direct aromatic iodination using iodine and nitrogen dioxide
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Direct iodination of a variety of aromatic compounds is achieved by using nitrogen dioxide as an oxidant in addition to iodine. The reaction affords aromatic monoidodides m high yields with high para-regioselectivity. 4,4'- Diiodo binuclear compounds are also obtained effectively by controlling the stoichiometry.
- Noda, Yumiki,Kashima, Mikito
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p. 6225 - 6228
(2007/10/03)
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- IODINATION OF ALKYLBENZENES WITH IODINE AND SILVER NITRITE
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Iodination of alkylbenzenes with iodine and silver nitrite at room temperature gives iodoalkylbenzenes in good yield.
- Sy, Wing-Wah,Lodge, Bruce A.
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p. 3769 - 3772
(2007/10/02)
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- Halogenation Using Quaternary Ammonium Polyhalides. XIV. Aromatic Bromination and Iodination of Arenes by Use of Benzyltrimethylammonium Polyhalides-Zinc Chloride System
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The reaction of arenes with benzyltrimethylammonium tribromide or benzyltrimethylammonium dichloroiodate in acetic acid in the presence of ZnCl2 at room temperature or at 70 deg C gave brome- or iodo-substituted arenes in good yield, respectively.
- Kajigaeshi, Shoji,Kakinami, Takaaki,Moriwaki, Masayuki,Tanaka, Toshio,Fujisaki, Shizuo,Okamoto, Tsuyoshi
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p. 439 - 443
(2007/10/02)
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- AROMATIC IODINATION WITH ALUMINUM AND COPPER (II) CHLORIDES AND IODINE
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Aryl iodides have been synthesized by a simple reaction of aromatic compounds with iodine and an equimolecular mixture of aluminum and copper(II) chlorides.The reaction is widely capable of application, especially to liquid aromatic substrates, with fair to excellent yields.
- Sugita, Toshio,Idei, Mitsushige,Ishibashi, Yoshiyuki,Takegami, Yoshinobu
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p. 1481 - 1484
(2007/10/02)
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- A Mild and Convenient Procedure for Conversion of Aromatic Compounds into Their Iodides Using Ammonium Hexanitratocerate(IV)
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Polymethylbenzenes, polymethoxybenzenes, and naphthalene are iodinated with tetrabutylammonium iodide, alkali metal iodides, or molecular iodine in the presence of ammonium hexanitrocerate(IV).Ammonium hexanitrocerate(IV) behaves as a catalyst in the latter system, whereas it is a reagent in the former two.
- Sugiyama, Takashi
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p. 2847 - 2848
(2007/10/02)
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