cas 348-52-7, 1-Fluoro-2-iodobenzene | Articles data

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Synthesis of biaryl compounds via Suzuki homocoupling reactions catalyzed by metal organic frameworks encapsulated with palladium nanoparticles
Heterogeneous homocoupling reactions of phenylboronic acids were greatly accelerated via Suzuki homocoupling reactions. In this work, a tandem route was designed which firstly one part of phenylboronic acids reacted with iodine to form iodobenzenes, then another part of phenylboronic acids coupled with iodobenzenes to produce biaryl compounds. The tandem reaction were catalyzed by a bifunctional heterogeneous catalyst of metal organic frameworks encapsulated with palladium nanoparticles (Pd?MOFs). This strategy for forming symmetric C-C bond between benzene rings has obvious advantages such as high efficiency, easy separation, good recyclability and no addition of toxic halogenated benzene.
Bao, Yan-Sai,Cui, Xin-Yu,Han, Zheng-Bo,Li, Xin,Tang, Hong,Yang, Ming,Zhang, Yu-Yang,Zhao, Kun,Zhou, Mei-Li
(2020/12/17)

Selective C-H Iodination of (Hetero)arenes
Iodoarenes are versatile intermediates and common synthetic targets in organic synthesis. Here, we present a strategy for selective C-H iodination of (hetero)arenes with a broad functional group tolerance. We demonstrate the utility and differentiation to other iodination methods of supposed sulfonyl hypoiodites for a set of carboarenes and heteroarenes.
Tanwar, Lalita,B?rgel, Jonas,Lehmann, Johannes,Ritter, Tobias
supporting information
p. 5024 - 5027
(2021/06/30)

Application of trivalent iodine compounds as catalysts in Bal-Schiemann reaction
The invention discloses an application of trivalent iodine compounds shown in formula I and/or II in the description and used as catalysts in Bal-Schiemann reaction. The trivalent iodine compounds areused as the catalysts in the Bal-Schiemann reaction, so that the Bal-Schiemann reaction can be conducted at room temperature or near room temperature when a thermochemical method is used, and the reaction has mild reaction conditions, wide substrate use range and short reaction time, and is safe and easy to operate, products are easy to separate, and raw materials are simple and low in toxicity.
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Paragraph 0153; 0158

(2018/10/19)

Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar-X σ-Bonds and Acid Chloride Synthesis
We describe the development of a new method to use palladium catalysis to form functionalized aromatics: via the metathesis of covalent σ-bonds between Ar-X fragments. This transformation demonstrates the dynamic nature of palladium-based oxidative addition/reductive elimination and offers a straightforward approach to incorporate reactive functional groups into aryl halides through exchange reactions. The reaction has been exploited to assemble acid chlorides without the use of high energy halogenating or toxic reagents and, instead, via the metathesis of aryl iodides with other acid chlorides.
De La Higuera Macias, Maximiliano,Arndtsen, Bruce A.
supporting information
p. 10140 - 10144
(2018/08/23)

Hypervalent Iodine(III)-Catalyzed Balz–Schiemann Fluorination under Mild Conditions
An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25–60 °C), and features a wide substrate scope and good functional-group compatibility.
Xing, Bo,Ni, Chuanfa,Hu, Jinbo
p. 9896 - 9900
(2018/07/31)

Expanding the Balz–Schiemann Reaction: Organotrifluoroborates Serve as Competent Sources of Fluoride Ion for Fluoro-Dediazoniation
The Balz–Schiemann reaction endures as a method for the preparation of (hetero)aryl fluorides yet is eschewed due to the need for harsh conditions or high temperatures along with the need to isolate potentially explosive diazonium salts. In a departure from these conditions, we show that various organotrifluoroborates (RBF3?s) may serve as fluoride ion sources for solution-phase fluoro-dediazoniation in organic solvents under mild conditions. This methodology was successfully extended to a one-pot process obviating aryl diazonium salt isolation. Sterically hindered (hetero)anilines are fluorinated under unprecedentedly mild conditions in good-to-excellent yields. Taken together, this work expands the repertoire of RBF3?s to act as fluorine ion sources in an update to the classic Balz–Schiemann reaction.
Mohy El Dine, Tharwat,Sadek, Omar,Gras, Emmanuel,Perrin, David M.
supporting information
p. 14933 - 14937
(2018/09/25)

Electrochemical Synthesis of Aryl Iodides by Anodic Iododesilylation
An electrochemical access to iodinated aromatic compounds starting from trimethylsilyl-substituted arenes is presented. By design of experiments, highly efficient and mild conditions were identified for a wide range of substrates. A functional group stability test and the synthesis of an important 3-iodobenzylguanidine radiotracer illustrate the scope of this process.
M?ckel, Robert,Hille, Jessica,Winterling, Erik,Weidemüller, Stephan,Faber, Tabea Melanie,Hilt, Gerhard
supporting information
p. 442 - 445
(2018/02/21)

Utilising Sodium-Mediated Ferration for Regioselective Functionalisation of Fluoroarenes via C?H and C?F Bond Activations
Pairing iron bis(amide) Fe(HMDS)2 with Na(HMDS) to form new sodium ferrate base [(dioxane)0.5?NaFe(HMDS)3] (1) enables regioselective mono and di-ferration (via direct Fe?H exchange) of a wide range of fluoroaromatic substrates under mild reaction conditions. Trapping of several ferrated intermediates has provided key insight into how synchronised Na/Fe cooperation operates in these transformations. Furthermore, using excess 1 at 80 °C switches on a remarkable cascade process inducing the collective twofold C?H/threefold C?F bond activations, where each C?H bond is transformed to a C?Fe bond whereas each C?F bond is transformed into a C?N bond.
Maddock, Lewis C. H.,Nixon, Tracy,Kennedy, Alan R.,Probert, Michael R.,Clegg, William,Hevia, Eva
supporting information
p. 187 - 191
(2017/12/07)

Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide
A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.
Mukhopadhyay, Sushobhan,Batra, Sanjay
supporting information
p. 14622 - 14626
(2018/09/21)

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-catalysed aromatic-Finkelstein reactions with amine-based ligand systems
A new efficient and low-cost ligand, diethylenetriamine, has been utilised to promote the iodination of 16 different bromo-substrates via the copper catalysed Finkelstein halogen exchange reaction under mild conditions. In contrast to earlier methods, the use of inert atmosphere conditions was not required to obtain high yields and purity. Studies on the speciation of the catalyst in solution indicate rapid disproportionation of copper(i) in the presence of diethylenetriamine to give copper(0) and a bis-ligated copper(ii) complex which is characterised by X-ray diffraction. This copper(ii) complex was also shown to be catalytically active in the halogen exchange reaction. In contrast, no significant disproportionation was observed using dimethylethylenediamine as the ligand, and the solid-state structures of a copper(i) dimeric complex and a 2D polymeric network of copper(i) iodide tetramers are reported. The catalytic activity of diethylenetriamine and dimethylethylenediamine with both copper(i) and copper(ii) salts are compared, and possible mechanistic implications discussed.
Jin, Xiaodong,Davies, Robert P.
p. 2110 - 2117
(2017/07/22)

Diphenyliodonium-Catalyzed Fluorination of Arynes: Synthesis of ortho-Fluoroiodoarenes
Described is a one-pot vicinal fluorination-iodination of arynes at room temperature. The diphenyliodonium salt proved to be a privileged catalyst for this nucleophilic fluorination process using CsF as a fluorine source, and a subsequent facile electrophilic iodination with C4F9I was also found to be crucial to ensure the efficient fluorination. This new synthetic protocol has a broad substrate scope under mild reaction conditions.
Zeng, Yuwen,Li, Guangyu,Hu, Jinbo
supporting information
p. 10773 - 10777
(2015/09/15)

Cu-catalyzed couplings of aryl iodonium salts with sodium trifluoromethanesulfinate
A convenient method for the preparation of aryl trifluoromethylsulfones from the reactions of diaryliodonium salts with sodium trifluoromethanesulfinate in the presence of copper catalysts is described. Cuprous oxide in DMF was found to be the optimal catalyst for the reaction. The reaction conditions are tolerant of various functional groups as well as of various counteranions of the iodonium salt. The synthetic utility of the process is demonstrated by performing the reaction on a preparative scale (88 g).
Cullen, Steven C.,Shekhar, Shashank,Nere, Nandkishor K.
p. 12194 - 12201
(2014/01/06)

Synthesis of aryl fluorides on a solid support and in solution by utilizing a fluorinated solvent
(Figure Presented) F for fast: The perfluorinated solvent C 6F14 is the key to a new variant of the BalzSchiemann reaction for the synthesis of fluorinated arenes. Triazenes are converted into fluoroarenes under mild con-ditions on a support and in solution (see scheme). The method is straightforward and inexpensive, and yields previously difficult-to-prepare fluoroarenes in high purity.
Doebele, Marion,Vanderheiden, Sylvia,Jung, Nicole,Braese, Stefan
supporting information; experimental part
p. 5986 - 5988
(2010/10/01)

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)

Sulfur contamination due to quenching of halogenation reactions with sodium thiosulfate: Resolution of process problems via improved quench protocols
Many metal-mediated cross-couplings involve the use of organic halides, which are usually accessed by halogenation reactions. Cross-couplings are sensitive to the presence of impurities in the halides. This paper describes the origin of one such problematic impurity (sulfur) during the synthesis of organic halides and proposes alternatives to minimize or eliminate its formation.
Xiang, Yanqiao,Caron, Pierre-Yves,Lillie, Brett M.,Vaidyanathan, Rajappa
p. 116 - 119
(2012/12/31)

Efficient copper-catalyzed N-arylation of sulfoximines with aryl iodides and aryl bromides
Two simple and inexpensive systems for copper-catalyed N-arylations of sulfoximines with aryl bromides and aryl iodides have been developed. Using 10 mol % of a copper(I) salt in combination with 20 mol % of a 1,2-diamine and Cs2CO3 provides N-arylated sulfoximines in high yields. Various functional groups and heteroatoms are tolarated. The method is complementary to the known protocols for N-arylations of sulfoximines, which require stoichiometric quantities of copper salts or cost-intensive palladium/BINAP catalysts.
Sedelmeier, Joerg,Bolm, Carsten
p. 6904 - 6906
(2007/10/03)

Method for producing tetrakis ( fluoroaryl) borate-magnesium compound
Fluoroaryl magnesium halide is reacted with a boron compound so that a molar ratio of the fluoroaryl magnesium halide to the boron compound is not less than 3.0 and not more than 3.7, so as to produce a tetrakis (fluoroaryl) borate·magnesium compound. With this method, there occurs no hydrogen fluoride which corrodes a producing apparatus and requires troublesome waste water treatment.
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(2008/06/13)

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A new ortho functionalisation of flouro- and ethylbenzene involving a 2,5- disilylation with trimethylcholorsilane in the presence of lithium in THF is reported. After aromatisation, electrophilic substitution of the TMS group in position 2, desilylation in position 5, ortho acetyl-, benzoyl-, bromo-and iodo- fluorobenzenes and ethylbenzenes are obtained in good yields.
Bennetau, Bernard,Krempp, Michele,Dunogues, Jacques,Ratton, Serge
p. 6179 - 6182
(2007/10/02)

Generation of ortho-Potassiofluorobenzene and its Functionalization
A number of ortho-substituted fluorobenzenes are readily accessible by treating fluorobenzene at -100 deg C with 1:1 molar mixture of potassium tert-butoxide and n-butyllithium in tetrahydrofuran and hexane, and subsequently adding an electrophilic reagent.
Fossatelli, M.,Verkruijsse, H.D.,Brandsma, L.
p. 1701 - 1704
(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)

Lower Nitrogen Oxide Species as Catalysts in a Convenient Procedure for the Iodination of Aromatic Compounds
A simple method for the iodination of aromatic compounds, using I- as the iodine source and the O2 and catalytic amounts of NO+BF4- as the oxidant, is presented.The reactions are performed at 25 deg C in CF3COOH/CH2Cl2 or CF3COOH/CH3COOH mixtures and compounds with as different reactivities as the halobenzenes and 1-methoxynaphthalene can be iodinated in very good yields.A set of relative rates, isotope effects, and isomer distributions in accordance with the electrophilic action of an "I+" species are presented.The formation of "I+" is discussed in terms of possible outer-sphere and inner-sphere electron-transfer steps.Aromatic bromination and to a lesser extent chlorination can be performed by using similar methods.
Radner, Finn
p. 3548 - 3553
(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)

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)

POTASSIUM PERMANGANATE - A CONVENIENT OXIDANT FOR DIRECT IODINATION OF AROMATIC COMPOUNDS.
The authors propose the use of potassium permanganate for direct iodination of aromatic compounds. They tested an iodination system containing iodine, potassium permanganate, and sulfuric and nitric acids on a large number of aromatic compounds. Experimental results show that it is effective for iodination of benzene, halobenzenes, oxygen-containing arenes, alkylbenzenes, and certain condensed hydrocarbons. Iodide yields are often close to, or even higher than, those obtained with the use of periodic and iodic acids. Potassium permanganate has not been used previously for iodination of aromatic compounds, probably because in absence of additives its activating effect on iodine is very weak. However, the effectiveness of the reaction is raised sharply when sulfuric acid is added to the system. This is due both to the higher degree of ionization of iodine molecules, as the result of which the electrons of the I-I bond become more accessible to the oxidant, and to the higher oxidizing power of potassium permanganate in a strongly acidic medium.
Chaikovskii,Novikov
p. 121 - 123
(2007/10/02)

Preparation of arylalkanoic acids
A novel process for making aryl propionic acids is described. It comprises reaction of a Grignard compound, obtained from an aryl bromide and magnesium, with a lithium, sodium, magnesium or calcium salt of 2-bromopropionic acid, followed by acidification.
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(2008/06/13)