cas 583-55-1, 1-Bromo-2-iodobenzene | Articles data

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Preparation method 2 - bromoiodobenzene
The invention discloses a preparation method of 2 -bromoiodobenzene, which comprises the following steps: under the protection of inert gas, adding triphenylphosphine to an organic solvent, adding organic amine to 50 - 75 °C DEG C under stirring conditions, and stirring 1 - 2 hours. Then iodine is added to 60 - 80 °C thermal insulation stirring 2 - 4.5 hours. Finally 2 - bromophenol was added and stirred 5 - 10 hours under reflux. The resulting reaction solution was naturally cooled to ≤ 40 °C, sodium methoxide was added, stirred and filtered, and the filtrate was post-treated to give 2 - bromoiodobenzene. 2 - Bromoiodobenzene is prepared by the method disclosed by the invention, and has the characteristics of simple process and high product yield.
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Paragraph 0024-0037

(2021/08/25)

Mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen: Development of a base-catalyzed iododeboronation for radiolabeling applications
An investigation into the mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen reagents is reported. Evidence is provided to show that this takes place via a boronate-driven ipso-substitution pathway and that Cu is not required for these processes to operate: General Lewis base catalysis is operational. This in turn allows the rational development of a general, simple, and effective base-catalyzed halodeboronation that is amenable to the preparation of 125I-labeled products for SPECT applications.
Molloy, John J.,O'rourke, Kerry M.,Frias, Carolina P.,Sloan, Nikki L.,West, Matthew J.,Pimlott, Sally L.,Sutherland, Andrew,Watson, Allan J. B.
supporting information
p. 2488 - 2492
(2019/04/10)

Metathesis-active ligands enable a catalytic functional group metathesis between aroyl chlorides and aryl iodides
Current methods for functional group interconversion have, for the most part, relied on relatively strong driving forces which often require highly reactive reagents to generate irreversibly a desired product in high yield and selectivity. These approaches generally prevent the use of the same catalytic strategy to perform the reverse reaction. Here we describe a catalytic functional group metathesis approach to interconvert, under CO-free conditions, two synthetically important classes of electrophiles that are often employed in the preparation of pharmaceuticals and agrochemicals—aroyl chlorides (ArCOCl) and aryl iodides (ArI). Our reaction design relies on the implementation of a key reversible ligand C–P bond cleavage event, which enables a non-innocent, metathesis-active phosphine ligand to mediate a rapid aryl group transfer between the two different electrophiles. Beyond enabling a practical and safer approach to the interconversion of ArCOCl and ArI, this type of ligand non-innocence provides a blueprint for the development of a broad range of functional group metathesis reactions employing synthetically relevant aryl electrophiles.
Lee, Yong Ho,Morandi, Bill
p. 1016 - 1022
(2018/09/06)

Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids
A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids has been developed, and the corresponding aryl iodides were obtained in good yields. The method shows some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.
Jiang, Min,Yang, Haijun,Jin, Yunhe,Ou, Lunyu,Fu, Hua
supporting information
p. 1572 - 1577
(2018/06/26)

Copper-Free Double Silylation of 1,2-Dibromobenzenes Using a Mg/LiCl/DMI System
The reaction of 1,2-dibromobenzenes with chlorotrimethylsilane efficiently proceeded in the presence of Mg and LiCl in DMI under mild conditions, giving 1,2-bis(trimethylsilyl)benzenes in good to high yields. The reaction of 1,2-dibromobenzenes with chlorodimethylsilane under the same conditions afforded the corresponding 1,2-bis(dimethylsilyl)benzenes in high yields. Functional group transformations of 1,2-bis(trimethylsilyl)benzene were conducted to demonstrate the synthetic utility.
Kitamura, Tsugio,Yamada, Rin,Gondo, Keisuke,Eguchi, Nobuo,Oyamada, Juzo
p. 2495 - 2500
(2017/05/22)

LIGHT-EMITTING MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE, ORGANIC ELECTROLUMINESCENT DEVICE USING SAME, AND MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE
Disclosed are a novel aromatic compound having excellent light emitting efficiency and thermal stability, a manufacturing method thereof, and an organic electroluminescent device comprising the novel aromatic compound. According to the present invention, provided are an aromatic compound forming a ring, and a novel aromatic derivative represented by chemical formula 1, which improves performance of a device. In the chemical formula 1, Z is equally or differently N (nitrogen), O (oxygen), or S (sulfur) in each case. Also, when Z is N (nitrogen), L1 is an integer of 1, and when Z is O (oxygen) or S (sulfur), L1 is an integer of 0.COPYRIGHT KIPO 2015
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Paragraph 0142-0144

(2016/10/08)

A practical and general ipso iodination of arylboronic acids using N-iodomorpholinium iodide (NIMI) as a novel iodinating agent: mild and regioselective synthesis of aryliodides
A mild and efficient protocol for the ipso-iodination of aryl boronic acids using N-iodomorpholinium iodide (NIMI) generated in situ from morpholine and molecular iodine as a novel iodinating agent has been developed. The addition of a catalytic amount of copper iodide found to promote rate enhancement of the iodination reaction and dramatic increase in the yield depending upon the nature of the boronic acid was observed. The mechanistic study revealed that depending upon the nature of the substrate, either the classical ipso substitution or copper catalysed iododeborylation pathway overall dominates the present iodination reaction. The features such as mild reaction conditions, operational simplicity, high to excellent yields, excellent functional group compatibility and low catalyst loading make this method potentially useful in organic synthesis.
Tale,Toradmal,Gopula
p. 84910 - 84919
(2015/10/28)

Tribromoisocyanuric acid in trifluoroacetic acid: An efficient system for smooth brominating of moderately deactivated arenes
Moderately deactivated arenes are efficiently brominated by the reaction with tribromoisocyanuric acid (0.34 mol equiv) in trifluoroacetic acid at room temperature in 48-85% isolated yield. This medium avoids the polybromination of the substrate, observed in the same reaction performed in 98% H 2SO4. Georg Thieme Verlag Stuttgart · New York.
De Almeida, Leonardo S.,De Mattos, Marcioc. S.,Esteves, Pierre M.
p. 603 - 606
(2013/04/10)

Bromination of aromatic compounds using an Fe2O 3/zeolite catalyst
The catalytic bromination of non-activated aromatic compounds has been achieved using an Fe2O3/zeolite catalyst system. FeBr 3 was identified as the catalytic species, formed in situ from HBr and Fe2O3. The catalyst was easy-to-handle and cost effective and could also be recycled. The reaction system was also amenable to the one-pot sequential bromination/C-C bond formation of benzene.
Nishina, Yuta,Takami, Keishi
supporting information
p. 2380 - 2383
(2013/02/21)

A facile synthesis of indolo[3,2,1-jk]carbazoles via palladium-catalyzed intramolecular cyclization
A new efficient synthesis of indolo[3,2,1-jk]carbazoles by the palladium-catalyzed cyclization of N-(2-bromoaryl)carbazoles is described. The reaction involves intramolecular C-C bond formation, coupled with the cleavage of a C-X bond and a C-H bond on carbazole ring. Substitutions on N-aryl core with either electron-donating or electron-withdrawing groups are introduced, and different reaction factors for cyclization are evaluated.
Lv, Jun,Liu, Qiancai,Tang, Jie,Perdih, Franc,Kranjc, Kristof
supporting information
p. 5248 - 5252
(2012/10/30)

Rhodium(III)-catalyzed oxidative ciH coupling of N-methoxybenzamides with aryl boronic acids: One-pot synthesis of phenanthridinones
General solution: An efficient rhodium-catalyzed dual CiH bond activation and cyclization of N-methoxybenzamides 1 with aryl boronic acids 2 (see scheme; Cp=Me5C5) provides a straightforward and general approach to the phenanthridinone structure, which occurs widely in natural products and drugs. Highly regioselective CiC and CiN bond formation under mild conditions afforded a wide range of substituted phenanthridinones 3. Copyright
Karthikeyan, Jaganathan,Haridharan, Radhakrishnan,Cheng, Chien-Hong
supporting information
p. 12343 - 12347
(2013/02/23)

Allylic carbon-carbon double bond directed pd-catalyzed oxidative ortho -olefination of arenes
Pd-catalyzed selective ortho-olefination of arenes assisted by an allylic C-C double bond at room temperature using O2 as a terminal oxidant is described. A possible mechanism involving the initial coordination of allylic C=C bond to Pd followed by selective o-C-H bond metalation is proposed.
Gandeepan, Parthasarathy,Cheng, Chien-Hong
supporting information; experimental part
p. 5738 - 5741
(2012/05/07)

Tetraflic acid (1,1,2,2-Tetrafluoroethanesulfonic acid, HC 2F4SO3H) and gallium tetraflate as effective catalysts in organic synthesis
Tetraflic acid offers ample acidity for various organic reactions that require high acidity. Its gallium(III) salt is an efficient catalyst under mild condtions for synthetic transformations such as the ketonic Strecker reaction for the synthesis of fluorinated α-amino nitriles and condensation- cyclzation reactions using suitable fluoro ketones and 1,2-disubstituted benzenes for the direct preparation of 5-membered or 6-membered fluorinated heterocycles. Copyright
Prakash, G. K. Surya,Mathew, Thomas,Panja, Chiradeep,Kulkarni, Aditya,Olah, George A.,Harmer, Mark A.
p. 2163 - 2171
(2012/11/07)

PROCESS FOR THE PREPARATION OF IODIDES
This invention is directed to a process for the preparation of high yield alkyl or aryl iodide from its corresponding carboxylic acid using N-iodo amides.
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(2012/01/05)

Fluoradenes via palladium-catalyzed intramolecular arylation
A novel approach towards 7b-aryl-indeno[1,2,3-jk]fluorene based on a nitrogen-containing core is reported. The acid-promoted Friedel-Crafts reaction of 9-(2-bromophenyl)-9-fluorenol with carbazole, triphenylamine or triindole afforded 9-(2-bromophenyl)fluorenyl-carbazole, -triphenylamine and -triindole derivatives, which were subsequently converted to 7b-aryl-fluoradenes via palladium-catalyzed intramolecular C-H direct arylation as a key step.
Rong, Lingling,Liu, Qiancai,Shi, Yingbo,Tang, Jie
supporting information; experimental part
p. 2155 - 2157
(2011/03/22)

Superelectrophilic iodination of deactivated arenes with triiodoisocyanuric acid
The reaction of triiodoisocyanuric acid (TICA) with deactivated arenes in acidic medium led to the efficient and regioselective formation of the corresponding iodoarenes, in 55-88% isolated yield. The acidity of the medium was found to be the most important factor influencing the electrophilic iodination of weakly nucleophilic substrates by TICA. Georg Thieme Verlag Stuttgart New York.
Da Ribeiro, Rodrigo S.,Esteves, Pierre M.,De Mattos, Marcio C. S.
experimental part
p. 739 - 744
(2011/04/24)

Metal-free efficient, general and facile iododecarboxylation method with biodegradable co-products
The development of a novel, efficient and robust method for the general conversion of aliphatic and aromatic carboxylic acids to organic iodides without the use of heavy metals or strong oxidizing agents is reported. Commercially available N-iodoamides were used for both initiation and halogen donation under irradiative conditions. Isolation of the product is extremely simple and the major co-product is removed as a water-soluble biodegradable material. Copyright
Kulbitski, Kseniya,Nisnevich, Gennady,Gandelman, Mark
supporting information; experimental part
p. 1438 - 1442
(2011/07/30)

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)

METHOD OF PRODUCING IODIZING AGENT, AND METHOD OF PRODUCING AROMATIC IODINE COMPOUND
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)

IBX-I2 redox couple for facile generation of IOH and I +: Expedient protocol for iodohydroxylation of olefins and iodination of aromatics
(Chemical Equation Presented) IBX is readily reduced to IBAin the presence of molecular iodine in DMSO to generate hypoiodous acid (IOH), which reacts with a variety of olefins as well as R, β-unsaturated ketones leading to their respective iodohydrins with anti stereochemistry. The same redox chemistry in acetonitrile containing TFA produces iodonium ions for facile iodination of a variety of aromatic compounds in respectable isolated yields.
Moorthy, Jarugu Narasimha,Senapati, Kalyan,Kumar, Sarvesh
supporting information; experimental part
p. 6287 - 6290
(2009/12/08)

Direct synthesis of iodoarenes from aromatic substrates using molecular iodine
Easy laboratory procedures for oxidative iodination of aromatic substrates are presented. One procedure includes the iodination using molecular iodine, concentrated sulfuric acid, and potassium peroxodisulfate, and another uses a reagent system containing molecular iodine, potassium peroxodisulfate, and trifluoroacetic acid. These procedures are especially effective for benzene and less deactivated aromatic substrates, such as halobenzenes, trifluoromethylbenzene, and benzoic acid. Georg Thieme Verlag Stuttgart.
Hossain, Md. Delwar,Oyamada, Juzo,Kitamura, Tsugio
p. 690 - 692
(2008/09/21)

Halogen-metal exchange in 1,2-dibromobenzene and the possible intermediacy of 1,2-dilithiobenzene
(Chemical Equation Presented) The one-step high-yield synthesis of 1,2-bis(trimethylsilyl)-benzene from 1,2-dibromobenzene using tert-butyllithium and trimethylsilyltriflate is reported. A mechanistic investigation shows that 1,2-dilithiobenzene is not an intermediate in this reaction; the coexistence of trimethylsilyltriflate and tert-butyllithium at very low temperatures allows a sequence of bromine-lithium exchange and subsequent derivatization reactions to operate.
Bettinger, Holger F.,Filthaus, Matthias
p. 9750 - 9752
(2008/03/17)

N-halosuccinimide/BF3-H2O, efficient electrophilic halogenating systems for aromatics
N-Halosuccinimides (NXS, 1) are efficiently activated in trifluoromethanesulfonic acid and BF3-H2O, allowing the halogenations of deactivated aromatics. Because BF3-H2O is more economic, easy to prepare, nonoxidizing, and offers sufficiently high acidity (-H0 ≈ 12, only slightly lower than that of trifluoromethanesulfonic acid), an efficient new electrophilic reagent combination of NXS/BF3-H2O has been developed. DFT calculations at the B3LYP/6-311++G**//B3LYP/6-31G* level suggest that protonated N-halosuccinimides undergo further protosolvation at higher acidities to reactive superelectrophilic species capable either in the transfer of X+ from the protonated forms of NXS to the aromatic substrate or in forming a highly reactive and solvated X+ which would readily react with the aromatic substrates. Structural aspects of the BF 3-H2O complex have also been investigated.
Prakash, G. K. Surya,Mathew, Thomas,Hoole, Dushyanthi,Esteves, Pierre M.,Wang, Qi,Rasul, Golam,Olah, George A.
p. 15770 - 15776
(2007/10/03)

An Efficient, Catalytic, Aerobic, Oxidative Iodination of Arenes Using the H5PV2Mo10O40 Polyoxometalate as Catalyst
Iodination of arenes was carried out by reacting 1 equiv of arene substrate with 0.5 equiv of iodine under an oxygen atmosphere with H 5PV2Mo10O40 as oxidation catalyst. The synthesis is an inherently waste-free method for the preparation of iodoarenes.
Branytska, Olena V.,Neumann, Ronny
p. 9510 - 9512
(2007/10/03)

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
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
p. 339 - 345
(2007/10/03)

Silicon directed ipso-substitution of polymer bound arylsilanes: Preparation of biaryls via the Suzuki cross-coupling reaction
A method for attaching haloarylsilanes to polymer support was developed. The polymer bound arylhalide were reacted with a variety of ArB(OH)2 under the Suzuki cross-coupling reaction conditions and the coupled resins were cleaved by different electrophiles to give ipso-substitution products in good yields.
Han, Yongxin,Walker, Shawn D.,Young, Robert N.
p. 2703 - 2706
(2007/10/03)

A Novel Aromatic Iodination Method Using F2
A new method for direct aromatic iodination with IF, made in situ from the corresponding elements, is described.Depending on the reaction time and temperature, mono- or polyiodination can be achieved.Even deactivated aromatic rings can be directly iodinated without the presence of any Friedel-Crafts catalyst.Sensitive groups such as aromatic aldehydes are not affected by the reagent.
Rozen, Shlomo,Zamir, Dov
p. 3552 - 3555
(2007/10/02)

CATALYTIC AND STOICHIOMETRIC BROMINATION OF AROMATIC COMPOUNDS IN AQUEOUS TRIFLUOROACETIC ACID IN THE PRESENCE OF NITROGEN-CONTAINING OXIDIZING AGENTS
The mono- and polybromination of benzene, halogenobenzenes, toluene, p-xylene, anisole, biphenyl, benzotrifluoride, benzoic acid, p-nitro- and p-carboxytoluene, p-methoxybenzonitrile, tetralin, and naphtalene were studied in trifluoroacetic acid and its aqueous solutions in systems containing stoichiometric amounts of bromine or alkali-metal bromide and stoichiometric or catalytic (in the presence of oxygen or air) amounts of nitrogen-containing oxidizing agent (nitrogen(IV) oxide, alkali-metal nitrate or nitrite).It is suggested that the brominating agent under the investigated conditions is nitryl bromide NO2Br.Under the conditions of catalytic bromination anthracene is oxidized to anthraquinone with a preparative yield.
Cheprakov, A. V.,Makhon'kov, D. I.,Rodkin, M. A.,Beletskaya, I. P.
p. 217 - 223
(2007/10/02)

STOICHIOMETRIC AND CATALYTIC OXIDATIVE IODINATION OF AROMATIC COMPOUNDS IN THE PRESENCE OF NITROGEN-CONTAINING OXIDIZING AGENTS IN AQUEOUS TRIFLUOROACETIC ACID
The conditions for oxidative monoiodination of benzene, halogenobenzenes, toluene, halogenotoluenes, and p-toluic acid in solvents based on trifluoroacetic acid were studied.Yields of the respective iodoarenes close to quantitative were obtained in systems containing 10-20 vol. percent of water in the solvent with equimolar amounts of alkali-metal metal iodides in relation to the substrate in the presence of stoichiometric (under anaerobic conditions) or catalytic (in the presence of oxygen or air) amounts of alkali-metal nitrates.The analogous reactions with nitrites can only be conducted under aerobic conditions.These iodinating systems are compared with systems based on acetic acid containing iodine and mixtures of sulfuric and nitric acids.The conditions for the iodination of toluene and for the transformations of the obtained iodotoluenes in the presence of nitrogen-containing oxidizing agents in trifluoroacetic acid solutions were studied in detail.It was shown that p-iodotoluene undergoes ipso-nitrodeiodination to a significant degree under these conditions.It is supposed that the iodinating agent in the investigated systems is trifluoroacetyl hypoiodite.Data on the assignment of the PMR spectra of the synthesized isomeric nitroiodotoluenes and chloroiodotoluenes by a simple additive method are given.
Makhon'kov, D. I.,Cheprakov, A. V.,Beletskaya, I. P.
p. 2029 - 2035
(2007/10/02)

Vapour-phase Chemistry of Arenes. Part 13. Reactivity and Selectivity in the Gas-phase Reactions of Hydroxyl Radicals with Monosubstituted Benzenes at 563 K
The reactions of hydroxyl radicals with benzene derivates C6H5Z (Z = H, Me, F, Cl, Br, I, CF3, or CN) have been studied in a flow reactor at 563 K in nitrogen, using the thermolysis of ButOOH as a source of .OH.Under these conditions there are two product-forming pathways.The major one involves hydrogen abstraction to give aryl radicals ZC6H4. (II) as the first step; depending on Z, its displacement to form phenol may also occur.Relative rates for hydrogen abstraction were determined in competition experiments using side-chain hydrogen abstraction from added toluene as a reference.This resulted in the order (for Z =): 1,8(Me), 1.0(H), 0.47(F), 0.29(Cl), 0.34(CF3), 0.20(CN), consonant with the electrophilic nature of .OH.The site selectivity of hydrogen abstractions was determined by scavenging part of the aryl radicals (II) with iodine.A Hammett plot, using ? constants for meta and para positions, led to ρ -1.0.The features of hydrogen abstraction by .OH are discussed and compared with those for the analogous reaction of Cl.The formation of phenol was found to decrease in importance in the order F, Cl, Br, and I.This result is rationalized on a thermochemical kinetic basis.
Mulder, Peter,Louw, Robert
p. 1167 - 1174
(2007/10/02)

OXIDATIVE HALOGENATION OF AROMATIC COMPOUNDS IN THE Pb3O4-Hal--CF3CO2H SYSTEM
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Makhon'kov, D. I.,Cheprakov, A. V.,Rodkin, M. A.,Serguchev, Yu. A.,Davydova, V. G.,Beletskaya, I. P.
p. 2424 - 2426
(2007/10/02)

Palladium-Catalyzed Coupling of Aryl Halides with (Trimethylstannyl)diphenylphosphine and (Trimethylsilyl)diphenylphosphine
The palladium-catalyzed reaction of aryl halides with either (trimethylsilyl)diphenylphosphine or (trimethylstannyl)diphenylphosphine gives aryldiphenylphosphines in good yields, under relatively mild conditions (50-70 deg C, benzene).The reaction tolerates a number of functional groups including methyl ethers, esters, ketones, nitriles, anilides, and certain halogens.The nitro and aldehyde groups as well as compounds containing groups such as amino and hydroxyl are not tolerated.
Tunney, S. E.,Stille, J. K.
p. 748 - 753
(2007/10/02)

OXIDATION BY METAL SALTS. OXIDATIVE HALOGENATION OF BENZENE AND HALOBENZENES PROMOTED BY Co(III) AND Mn(III) ACETATES IN TRIFLUOROACETIC ACID AND ITS AQUEOUS SOLUTIONS
A study was carried out on the oxidation of benzene and halobenzenes by Co(III) and Mn(III) acetates in the presence of alkali metal chlorides and bromides in CF3CO2H and its aqueous solutions (10-33 vol. percent H2O).The optimal water content in the solution is a function both of the nature of the metal oxidizing agent and the aromatic substrate.The reaction presumably proceeds through the formation of an aromatic radical-cation which then reacts with the halide anion.The oxidative chlorination of bromobenzene is complicated by ipso substitution and bromine redistribution.Phenyl iodosodichloride may be isolated in preparative yield in the chlorination of iodobenzene.In other cases, variation of the reaction conditions may give high yields of the corresponding chlorine and bromine derivatives.The feasibility of polychlorination was studied.Possible reaction mechanisms were considered.
Makhon'kov, D. I.,Cheprakov, A. V.,Beletskaya, I. P.
p. 609 - 615
(2007/10/02)

OXIDATION BY THE SALTS OF METALS. VI. OXIDATIVE IODINATION OF AROMATIC SUBSTRATES, PROMOTED BY Co(III), Mn(III), AND Ce(IV) COMPOUNDS IN AQUEOUS TRIFLUOROACETIC ACID
The direct iodination of benzene, halogenobenzenes, and p-methoxycarbonyltoluene in trifluoroacetic acid and its aqueous solutions with iodine or alkali-metal iodides was studied in the presence of Co(III) and Mn(III) acetates and ammonium cerium(IV) sulfate, which make it possible to obtain the respective iodoarenes with high yields under mild conditions.In the case of toluene the reaction is complicated by the formation of α-oxidation products.It is assumed that the iodinating agent is trifluoroacetyl hypoiodite, formed as a result of the oxidation of the iodine by the salt of the metal having variable valence.The highest yields of the iodoarenes were obtained with 90percent aqueous trifluoroacetic acid.
Makhon'kov, D. I.,Cheprakov, A. V.,Rodkin, M. A.,Beletskaya, I. P.
p. 1003 - 1006
(2007/10/02)

OXIDATIVE BROMINATION OF AROMATIC COMPOUNDS IN THE KBr-Pb(OAc)4-CF3CO2H SYSTEM
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Serguchev, Yu. A.,Davydova, V. G.,Makhon'kov, D. I.,Beletskaya, I. P.
p. 1550
(2007/10/02)

A Simple and General Route to Aryl Iodides from Arenes
Mercury(II) oxide-tetrafluoroboric acid reacts with arenes under mild or very mild conditions to afford, after treatment with iodine in a 'one-stage' reaction, the corresponding aryl iodide.The orientation is that expected based on general aromatic substitution theory and hence the meta-iodinated derivatives of deactivated arenes are accessible.
Barluenga, Jose,Campos, Pedro J.,Gonzalez, Jose M.,Asensio, Gregorio
p. 2623 - 2624
(2007/10/02)

Oxidative Displacement of Halogen from Alkyl Halides by Phenyliodine(III) Dicarboxylates
The reaction of alkyl iodides with aryliodine(III) dicarboxylates affords as the main product the ester derived through substitution of iodine by an acyloxy group; in some cases α-iodoalkyl esters are also formed along with other minor products.Certain reactive bromides and chlorides react along similar lines.The mechanism of these reactions is briefly discussed.
Gallos, John,Varvoglis, Anastasios
p. 1999 - 2002
(2007/10/02)

REACTIONS OF ARYLIODINE(III) DICARBOXYLATES WITH HALOGENS AND WITH BORON AND ALUMINIUM HALIDES. GENERATION OF ACYL HYPOHALITES AND HALOGENATION OF AROMATIC COMPOUNDS.
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Gallos, John,Varvoglis, Anastasios
p. 1649 - 1660
(2007/10/02)

AROMATIC IODINATION WITH ALUMINUM AND COPPER (II) CHLORIDES AND IODINE
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
p. 1481 - 1484
(2007/10/02)