- Efficient synthesis of 2-iodo and 2-dicyanomethyl derivatives of thiophene, selenophene, tellurophene, and thieno[3,2-b]thiophene
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An effective synthesis of 2-iodothiophene, 2-iodotellurophene, and 2-iodothieno[3,2-b]thiophene and a Pd-catalyzed carbon-carbon coupling reaction of these iodo derivatives as well as 2-iodoselenophene with malononitrile affording novel thienyl-, tellurienyl-, thieno[3,2-b]thienyl-, and selenienybnalononitrile are described. These heteroarylmalononitriles are important synthons for the preparation of 2-dicyanomethylene-2,5-dihydroheterophene chromophores.
- Takahashi, Kazuko,Tarutani, Shinji
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- ELECTROCATALYSE PAR DES COMPLEXES DU NICKEL DE LA SYNTHESE D'IODURES AROMATIQUES OU VINYLIQUES A PARTIR DE DERIVES BROMES CORRESPONDANTS
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In the solvent N-methyl-2-pyrrolidone the electrochemical reduction of nickel bromide in the presence of potassium iodide, leads to Ni(O) species which are very efficient in the catalytic halogen exchange.Conversion of non-activated aromatic bromides into the corresponding iodides is achieved in good yields, specially when anisole is added to the medium.
- Meyer, Gilbert,Rollin, Yolande,Perichon, Jacques
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- Sodium-mediated magnesiation of thiophene and tetrahydrothiophene: Structural contrasts with furan and tetrahydrofuran
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Metallation of sulfur heterocycles; Alkali-metal-mediated magnesiation has been employed to regioselectively metallate the S-heterocycles thiophene and tetrahydrothiophene at ambient temperature. The structural chemistry of the metallo-compounds is remark
- Blair, Victoria L.,Kennedy, Alan R.,Mulvey, Robert E.,O'Hara, Charles T.
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Read Online
- Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent
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Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined.
- Iioka, Ryoya,Yorozu, Kohei,Sakai, Yoko,Kawai, Rika,Hatae, Noriyuki,Takashima, Katsuki,Tanabe, Genzoh,Wasada, Hiroaki,Yoshimatsu, Mitsuhiro
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supporting information
p. 1553 - 1558
(2021/02/26)
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- Copper-promoted cyanation of aryl iodides with N,N-dimethyl aminomalononitrile
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A copper-promoted cyanation of aryl iodides has been successfully developed by using N,N-dimethyl aminomalononitrile as the cyanide source with moderate toxicity and better stability. This reaction features broad substrate scope, excellent reaction yields, readily available catalyst, and simple reaction conditions.
- Liu, Si-Zhan,Li, Jing,Xue, Cao-Gen,Xu, Xue-Tao,Lei, Lin-Sheng,Huo, Chen-Yu,Wang, Zhen,Wang, Shao-Hua
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supporting information
(2021/02/01)
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- Solvent-Free and Liquid-Phase Iodination of Thiophene Derivatives with Potassium Dichloroiodate Monohydrate
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Iodination of a series of benzene and thiophene derivatives by potassium dichloroiodate monohydrate was studied with and without a solvent. The liquid substrates tend to be more reactive in water while the solid substrates afford better yields in dichloromethane or under the solvent-free conditions. The 2-substituted thiophenes show good to excellent yields whereas the yield for 3-substituted and 3,4- or 2,4-disubstituted thiophenes and benzene derivatives are significantly lower. The mechanochemical reaction of 5-carbaldehyde-2,2′-bithiophene shows excellent yields, while 2,2′-bithiophene gives practical yields only in dichloromethane. In the case of thiophene and N -acetyl- p -toluidine, electrophilic iodination is accompanied by a small extent of chlorination.
- Hussain, Anwar,Sarkar, Akash Mamon,Sereda, Grigoriy,Zefirov, Nikolai
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p. 1140 - 1146
(2020/04/01)
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- Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations
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While halogenation is of key importance in synthesis and radioimaging, the currently available repertoire is largely designed to introduce a single halogen per molecule. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, outcompeting silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism.
- Deckers, Kristina,Fricke, Christoph,Schoenebeck, Franziska
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supporting information
p. 18717 - 18722
(2020/08/25)
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- Dehydroxyalkylative halogenation of C(aryl)-C bonds of aryl alcohols
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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
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supporting information
p. 7120 - 7123
(2020/07/14)
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- One of iodinated aromatic ring by iodine chloride in hydrochloric acid (by machine translation)
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[Problem] to one iodine chloride is used, and, stably iodinated aromatic compound can be iodinated aromatic compound production. [Solution] water containing one iodine chloride hydrogen chloride, iodine chloride content of 30% by mass of the first mass % -70, 3 mass % -20 mass % aqueous solution of hydrogen chloride content in the preparing step, a process for preparing an aromatic compound as the reaction substrate, the reaction substrate as an aqueous solution of the mixture of aromatic compounds, as the reaction substrate of one iodine chloride by reacting an aromatic compound, iodinated aromatic compound obtained in the step, the iodinated aromatic compound. [Drawing] no (by machine translation)
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Paragraph 0077-0080
(2019/09/10)
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- Oligothienyl catenated germanes and silanes: Synthesis, structure, and properties
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The synthesis of two new groups of oligothienyl catenated silanes and germanes, Me5M2Thn (1a-b), Me5M2ThnM2Me5 (2a-c) (terminal), and ThnM2Me4Thn (3a-d) (internal) (M = Si, Ge; n = 2, 3; Th = 2- or 2,5-thienyl), is reported. The study of their structural parameters as well as of their spectral (NMR), electrochemical (CV) and optical (UV/vis absorbance, luminescence) properties has been performed in detail; in addition, the unexpected compound [Th2Si2Me4Th]2 (3a′) is also studied. Theoretical investigations have been performed for model compounds in order to establish structure-property relationships. The molecular structures of 2a (Me5Si2Th2Si2Me5), 2b (Me5Ge2Th2Ge2Me5), 3a (Th2Si2Me4Th2) and 3b (Th2Ge2Me4Th2) have been investigated by X-ray diffraction analysis. An effective conjugation with flattening of both Th planes in terminal 2a and 2b was observed. The main trends in the dependence of the optical and electrochemical properties on the structural parameters have been established. All of the compounds studied exhibit a strong emission within the 378-563 nm range, and the maximal quantum yield (up to 77%) is observed for the Si derivative 3a′. For the majority of the compounds, the quantum yields (20-30%) are significantly larger than for 2,2′-bi- and 2,2′:5′,5′′-terthiophenes. Due to their good emission properties, these compounds could be used to develop new materials with specific spectral properties.
- Zaitsev, Kirill V.,Lam, Kevin,Poleshchuk, Oleg Kh.,Kuz'Mina, Lyudmila G.,Churakov, Andrei V.
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supporting information
p. 5431 - 5444
(2018/04/23)
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- Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids
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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
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supporting information
p. 1572 - 1577
(2018/06/26)
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- Synthesis method of 2-thiopheneacetic acid
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The invention provides a synthesis method of 2-thiopheneacetic acid. The synthesis method comprises the following steps: by taking thiophene as a raw material, chloridizing, iodizing, condensing with diethyl malonate, and finally hydrolyzing and heating for decarboxylation, so that 2-thiopheneacetic acid is obtained. The synthesis method provided by the invention is simple to operate, reaction process can be easily controlled, a highly toxic reagent does not need to be used, safety coefficient is high, the adopted raw material is cheap and easily available, pollution is low, requirement on production equipment is low, production cost is low, produced 2-thiopheneacetic acid is white solid powder, purity is more than or equal to 99.0%, product quality is good, and yield is high, so that the synthesis method is applicable to industrial production.
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Paragraph 0030; 0053; 0054
(2017/01/26)
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- Clean and Efficient Iodination of Thiophene Derivatives
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Iodination of thiophene derivatives is realized using a simple, fast, and efficient methodology. Iodination of thiophene and 2- or 3-substituted or 3,4-disubstituted thiophenes with N-iodosuccinimide (NIS) activated with 4-toluenesulfonic acid in ethanol gives pure iodinated products that require no further purification.
- Grolleau, Jérémie,Frère, Pierre,Gohier, Frédéric
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p. 3901 - 3906
(2015/12/18)
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- Practical and efficient ipso-iodination of arylboronic acids via KF/I2 system
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A facile and effective iododeboronation of variously substituted aryl and heteroarylboronic acids through activation and subsequent ipso-introduction of iodine is presented. The use of KF and I2 at 80 °C in 1,4-dioxane furnishes iodinated compounds in high yields.
- Tramutola, Francesco,Chiummiento, Lucia,Funicello, Maria,Lupattelli, Paolo
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p. 1122 - 1123
(2015/02/19)
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- New approach to electrochemical iodination of arenes exemplified by the synthesis of 4-iodopyrazoles of different structures
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The two-stage electrosynthesis of 4-iodosubstituted pyrazole derivatives was performed. At the first stage, KIO3 was obtained at the Ni anode under the undivided galvanostatic conditions of electrolysis of an aqueous alkaline solution of KI (or I2) at the Ni anode. At the second stage, pyrazole and its derivatives were iodinated in the heterophase (H2O-CHCl3 (CCl4)) medium by the KIO3-KI (or KIO3-I2) system in the presence of H2SO4. The yields of iodopyrazoles were 74-92%. The electrochemical iodination of anisole, 2-methylpyrazole, and thiophene was carried out to form 4-iodoanisole (88% yield), 4,5-diiodo-2-methylimidazole (54% yield), and a mixture of 2-iodothiophene (60% yield) and 2,5-diiodothiophene (4% yield).
- Lyalin,Petrosyan
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p. 360 - 367
(2015/02/05)
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- Potassium-alkyl magnesiates: Synthesis, structures and Mg-H exchange applications of aromatic and heterocyclic substrates
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Using structurally well-defined dipotassium-tetra(alkyl)magnesiates, a new straightforward methodology to promote regioselective Mg-H exchange reactions of a wide range of aromatic and heteroaromatic substrates is disclosed. Contacted ion pair intermediates are likely to be involved, with K being the key to facilitate the magnesiation processes. This journal is
- Baillie, Sharon E.,Bluemke, Tobias D.,Clegg, William,Kennedy, Alan R.,Klett, Jan,Russo, Luca,De Tullio, Marco,Hevia, Eva
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supporting information
p. 12859 - 12862
(2014/12/11)
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- Green halogenation of aromatic heterocycles using ammonium halide and hydrogen peroxide in acetic acid solvent
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The green generation of X+ (X = Br, I) using hydrogen peroxide in aqueous acetic acid allows access to aromatic heterocyclic halides in yields and purities comparable to syntheses employing N-bromosuccinimide. In activated and unsubstituted thiophene rings, regioselectivity is quantitative for positions α to the sulfur; pyrroles also give quantitative reactions, at least initially. Deactivated rings, including furans and thiazoles, as well as thiophenes with strongly electron-withdrawing groups showed little to no reactivity under the conditions investigated. The reaction shows remarkable functional group tolerance (to alcohol, nitro, alkyl, halo, and carbonyl groups), as shown through reaction with substituted phenols. In all bromination reactions, reaction yields and regiochemistry were very similar to reactions involving N-bromosuccinimide in tetrahydrofuran solvent.
- D'Aleo, Danielle N.,Allard, Sheena R.,Foglia, Cassandra C.,Parent, Shawna L.M.,Rohr, David J.,Gottardo, Christine,MacKinnon, Craig D.
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p. 679 - 683
(2013/08/23)
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- Efficient indium-mediated dehalogenation of aromatics in ionic liquid media
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An efficient indium-mediated dehalogenation reaction of haloaromatics and haloheteroaromatics in ionic liquids has been studied. This method is simple and effective in the presence of [bmim]Br. Furthermore, this methodology is environmentally friendly compared with conventional ones.
- Canete, Alvaro F.,Salas, Cristian O.,Zacconi, Flavia C.
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p. 398 - 407
(2013/03/13)
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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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- Efficient iodination of aromatic compounds using potassium ferrate supported on montmorillonite
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Potassium ferrate impregnated on montmorillonite is a mild, cheap, and non-toxic reagent for the iodination of phenols, including naphthol, aromatic amines, and heterocyclic substrates in fair to excellent yields by a simple isolation procedure.
- Keipour, Hoda,Khalilzadeh, Mohammad A.,Mohtat, Bita,Hosseini, Abolfazl,Zareyee, Daryoush
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experimental part
p. 1427 - 1430
(2012/06/01)
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- Cobalt-catalyzed preparation of arylindium reagents from aryl and heteroaryl bromides
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A cobalt-bathophenanthroline catalyst has been developed for the direct preparation of a variety of arylindium reagents from the corresponding aryl and heteroaryl bromides in the presence of indium metal and lithium chloride. The thus-formed arylindium reagents undergo efficient palladium-catalyzed cross-coupling reactions with aryl iodides, tolerating various functional groups including hydroxy and free amino groups.
- Adak, Laksmikanta,Yoshikai, Naohiko
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experimental part
p. 7563 - 7568
(2011/11/12)
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- Deprotonative metalation of substituted benzenes and heteroaromatics using amino/alkyl mixed lithium-zinc combinations
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Different homoleptic and heteroleptic lithium-zinc combinations were prepared, and structural elements obtained on the basis of NMR spectroscopic experiments and DFT calculations. In light of their ability to metalate anisole, pathways were proposed to justify the synergy observed for some mixtures. The best basic mixtures were obtained either by combining ZnCl 2·TMEDA (TMEDA = N,N,N',N'tetramethylethylenediamine) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 3 equiv) or by replacing one of the tmp in the precedent mixture with an alkyl group. The reactivity of the aromatic lithium zincates supposedly formed was next studied, and proved to be substrate-, base-, and electrophile-dependent. The aromatic lithium zincates were finally involved in palladium-catalyzed cross-coupling reactions with aromatic chlorides and bromides.
- Snegaroff, Katia,Komagawa, Shinsuke,Chevallier, Floris,Gros, Philippe C.,Golhen, Stephane,Roisnel, Thierry,Uchiyama, Masanobu,Mongin, Florence
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experimental part
p. 8191 - 8201
(2010/09/11)
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- Regiospecific reductive elimination from diaryliodonium salts
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(Figure Presented) Out-of-plane steric bulk furnished by a cyclophane substituent on iodine(III) strongly destabilizes the transition state in the reductive elimination from diaryliodonium salts and leads to regiochemical control (dubbed SECURE), as is demonstrated by computational and experimental studies. This approach should be general for high-valent maingroup and transition metal ions. X=N3, OAc, PhO, CF3CH2O, SCN, PhS.
- Wang, Bijia,Graskemper, Joseph W.,Qin, Linlin,DiMagno, Stephen G.
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supporting information; experimental part
p. 4079 - 4083
(2010/08/07)
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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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Page/Page column 10
(2010/05/13)
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- Cascade iodination-fluorination synthesis of 2-fluorothiophene and 5-fluoro-2-thienyliodonium salts
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The first synthesis of fluorine-containing 2-thienyliodonium salts was accomplished using cascade iodination-fluorination. According to this methodology, thiophene is first converted to bis(2-thienyl)iodonium hexafluorophosphate using an electrophilic iodination reaction. Upon heating with potassium fluoride, this salt undergoes regioselective fluorination producing 2-fluorothiophene. 2-Fluorothiophene is then iodinated again to yield fluorothienyliodonium salts.
- Onys'ko, Petro P.,Kim, Tetyana V.,Kiseleva, Olena I.,Rassukana, Yuliya V.,Gakh, Andrei A.
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experimental part
p. 501 - 504
(2010/01/14)
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- Deprotonation of thiophenes using lithium magnesates
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Thiophene was regioselectively deprotonated at C2 on treatment with 1/3 equiv of Bu3MgLi in THF at room temperature. The lithium arylmagnesate formed was either trapped with electrophiles or cross-coupled in a 'one-pot' procedure with aryl halides under palladium catalysis. 2-Chlorothiophene and 2-methoxythiophene were similarly deprotonated at C5 under the same reaction conditions. The enhancement of the reactivity of the base using TMEDA was evidenced using 1H NMR spectroscopy.
- Bayh, Omar,Awad, Ha?an,Mongin, Florence,Hoarau, Christophe,Trécourt, Fran?ois,Quéguiner, Guy,Marsais, Francis,Blanco, Fernando,Abarca, Belén,Ballesteros, Rafael
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p. 4779 - 4784
(2007/10/03)
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- Regioselective iodination of activated arenes using phenyl trimethylammonium dichloroiodate in ionic liquid under microwave irradiation
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The regioselective iodination of activated arenes has been achieved in the presence of phenyltrimethylammonium dichloroiodate and ionic liquid. The reaction has been carried out by both conventional heating as well as by microwave irradiation. Copyright Taylor & Francis, Inc.
- Tilve, Rutuja D.,Kanetkar, Vinod R.
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p. 1313 - 1318
(2007/10/03)
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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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- Efficient copper-catalyzed N-arylation of sulfoximines with aryl iodides and aryl bromides
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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
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p. 6904 - 6906
(2007/10/03)
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- An Efficient, Catalytic, Aerobic, Oxidative Iodination of Arenes Using the H5PV2Mo10O40 Polyoxometalate as Catalyst
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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
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p. 9510 - 9512
(2007/10/03)
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- Solvent-Free Iodination of Arenes at Room Temperature
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Silica supported bismuth(III)nitrate pentahydrate [BNP-SiO2] was prepared under simple co-grinding condition. The iodination of aromatic compounds using BNP-SiO2 and molecular iodine under solvent-free conditions is described. The reaction occurred in the solid state at room temperature, yielding the corresponding mono-iodo derivative in good yields. However, less activated aromatics required longer reaction time with comparatively less yield.
- Alexander, Varughese M.,Khandekar, Amit C.,Samant, Shriniwas D.
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p. 1895 - 1897
(2007/10/03)
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- Iodination of activated arenes using silfen: An improved protocol
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A simple and direct method for the iodination of activated arenes, using molecular iodine and silfen (silica supported ferric nitrate nonahydrate) as an oxidant, is presented. The reactions are performed at 20°C in dichloromethane. The method provides an easy access to the corresponding iodinated products in good yields. The observed orientation effects are in agreement with those based on general aromatic electrophilic substitution theory.
- Tilve, Rutuja D.,Alexander, Varughese M.,Khadilkar, Bhushan M.
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p. 9457 - 9459
(2007/10/03)
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- Selective metallation of thiophene and thiazole rings with magnesium amide base
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The chemoselective magnesiation of thiophene and thiazole derivatives were reported using magnesium chloride. Organomagnesium compounds were used at relatively higher temperatures. The results showed that hydrogen-magnesium exchange reaction of thiophene derivatives with iPr2NMgCl proceeded selectively.
- Shilai, Manabu,Kondo, Yoshinori,Sakamoto, Takao
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p. 442 - 444
(2007/10/03)
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- New synthetic method for the polymerization of alkylthiophenes
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The polymerization of 2-iodo-3-alkylthiophenes using a Heck-type reaction with Pd(OAc)2/NBu4Br as catalytic system is reported leading to expected functionalized oligomers with good yields.
- Sevignon, Marc,Papillon, Julien,Schulz, Emmanuelle,Lemaire, Marc
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p. 5873 - 5876
(2007/10/03)
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- Mild preparation of haloarenes by ipso-substitution of arylboronic acids with N-halosuccinimides
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Aryl and heteroaryl boronic acids react with N-iodosuccinimide and N-bromosuccinimide to give the corresponding iodo-and bromo- arenes in good to excellent yields. The reaction is usually highly regioselective and yields only the ipso-substituted product. Esters of arylboronic acids react similarly, but less readily.
- Thiebes, Christoph,Prakash, G. K. Surya,Petasis, Nicos A.,Olah, George A.
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p. 141 - 142
(2007/10/03)
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- Reevaluation of benzyltrimethylammonium dichloroiodide, previously reported to be a selective iodinating agent
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Benzyltrimethylammonium dichloroiodate, previously reported as an iodinating agent of thiophenes, appears to be a selective chlorinating agent of both thienyl and furyl derivatives containing a carbonyl group.
- D'Auria,Mauriello
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p. 248 - 250
(2007/10/02)
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- Bis-(trifluoroacetoxy)iodobenzene-iodine system: An efficient and selective reagent for iodination of thiophene derivatives
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Bis-(trifluoroacetoxy)iodobenzene-iodine system is a good iodinating reagent of thiophene derivatives giving products with iodine atom in α-position on the thiophene ring.
- D'Auria,Mauriello
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p. 4883 - 4884
(2007/10/02)
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- Aromatic iodination of activated arenes and heterocycles with lead tetraacetate as the oxidant
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An easy, cheap and fairly quick laboratory method is presented for aromatic iodination of some highly activated arenes and heterocycles with molecular iodine in the presence of either pure lead tetraacetate dissolved in glacial acetic acid, or with the same oxidant but prepared in situ from Pb3O4 dissolved in hot AcOH/Ac2O prior to the iodination. 4-Bromo- and 2,4-dibromoanisoles are obtained from anisole by the respective oxidative bromination.
- Krassowska-Swiebocka,Lulinski,Skulski
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p. 926 - 928
(2007/10/02)
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- PHOTOCHEMICAL ARYLATION OF 2-IODO-5-NITROTHIOPHENE
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The arylation of 2-iodo-5-nitrothiophene by a photochemical process has been investigated.This compound, in contrast with the photochemical behaviour of 5-iodothiophene-2-carbonitrile, gives the corresponding aryl and heteroaryl derivatives in good yields on irradiation in the presence of various aromatic substrates (benzene, naphthalene, thiophene).The photochemical reaction of 2-iodo-5-nitrothiophene in the presence of phenylacetylene gives the corresponding substitution product on the alkyne.
- D'Auria, Maurizio
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p. 195 - 198
(2007/10/02)
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- Lower Nitrogen Oxide Species as Catalysts in a Convenient Procedure for the Iodination of Aromatic Compounds
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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
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p. 3548 - 3553
(2007/10/02)
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- Photochemical Synthesis of Phenyl-2-thienyl Derivatives
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The irradiation (in benzene solution) of 5-bromo- and 5-iodo-thiophene-2-carbaldehyde or the corresponding methyl ketones furnishes the corresponding 5-phenyl derivatives.The same reactivity for other halogenothiophenes is reported: 3,5-dibromothiophene-2-carbaldehyde furnishes the 3-bromo-5-phenyl-2-thienyl derivative while the corresponding di-iodo compound yields 3,5-diphenylthiophene-2-carbaldehyde.In contrast, 5-acetyl-2,3-di-iodothiophene furnishes only the photosubstitution pruduct at C-5.Generally the iodine-containing compounds are more reactive and more stable under the reaction conditions than ones bearing bromine, in agreement with previous reports on the corresponding furan photochemistry.
- Antonioletti, Roberto,Auria, Maurizio D',Onofrio, Franco D',Piancatelli, Giovanni,Scettri, Arrigo
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p. 1755 - 1758
(2007/10/02)
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- Preparation of 2-Chlorofuran and 2-Chlorothiophene from the Respective Furan and Thiophene Mercurials and Disulfur Dichloride
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2-Chloro- and 2-iodo-substituted furans and thiophenes (with no admixture of higher halogenated products) have been obtained from 2,2'-difurylmercury or 2,2'-dithienylmercury by the action of either a solution of freshly-redistilled S2Cl2 in carbon disulfide or an aqueous solution of KI3, in 60-70percent isolated yields. 2-Chlorofuran and 2-chlorothiophene may also be obtained by the direct action of either furan or thiophene on a mixture of HgCl2 and S2Cl2, in 50percent and 60percent isolated yields, respectively.
- Khodeir, Mohammed N. M.,Skulski, Lech,Wroczynski, Piotr
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p. 443 - 448
(2007/10/02)
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- Kinetics of Iodination of Thiophene and 2-Halothiophenes
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The effect of substituents (Cl, Br and I) at the 2-position upon the rate of iodination with iodine monochloride in hydrochloric acid of thiophene at the 5-position, in 50percent aqueous acetic acid, had been studied at different temperatures.The rates and activation parameters for the 2-iodothiophene indicate an inductomeric mode of electron release by the iodine atom.
- Nair, M. R.
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p. 417 - 418
(2007/10/02)
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- Process for preparing hypotensive 2-(4-aroylpiperazin-1-yl)-amino-6,7-dimethoxyquinazolines
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Certain 2-(4-aroylpiperazin-1-yl)-4-amino-6,7-dimethoxyquinazolines are prepared by a novel process wherein certain 2-(4-substituted-piperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline intermediates wherein said substituent is cyano, certain carbon-oxygen double bond containing groups or certain carbon-nitrogen double bond containing groups, are reacted with certain metalloaryl compounds followed by hydrolysis. The products are known hypotensive agents. Certain of the process intermediates are novel compounds.
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- Sulfonation of aromatic compounds in the presence of solvents
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A process for the sulfonation of aromatic compounds wherein an aromatic substance consisting of one or more aromatic compounds susceptible to the action of sulfur trioxide is formed into a reactant by admixture with one or more organic liquids, substantially inert to sulfur trioxide under the conditions of the process, which reactant is brought to boiling at a temperature not greater than 100° C under a pressure of from 0.1 mm Hg to atmospheric pressure, gaseous sulfur trioxide is introduced thereinto thereby causing it to continue to boil, the component or components of the reactant thus volatilized is or are reconverted to liquid in a heat-exchanger and recycled to the reaction chamber, and the pressure in the reaction chamber and the rate at which the gaseous sulfur trioxide is introduced into the reactant are controlled so as to ensure that there is always present in the reaction chamber an amount of volatilizable matter exceeding that amount volatilizable by the heat of reaction of the aromatic substance present in the reaction chamber with the gaseous sulfur trioxide in contact with said aromatic substance and that the temperature of the reaction mixture is a temperature of 100° C or below.
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