- Microwave-accelerated iodination of some aromatic amines, using urea-hydrogen peroxide addition compound (UHP) as the oxidant
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A fast and simple method for the oxidative iodination of some aromatic amines, under microwave irradiation, is reported, using diiodine and the the strongly H-bonded urea-hydrogen peroxide addition compound (H 2NCONH)2...H2O2, UHP) as the oxidant. The reactions were carried out in boiling CHCl3 under a reflux condenser to afford, within 10 minutes, the purified monoiodinated products in 40-80% yields.
- Sosnowski, Maciej,Skulski, Lech
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Read Online
- Microwave-accelerated or conventionally heated iodination reactions of some aromatic amines, using ortho-periodic acid as the oxidant
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A fast and simple method for the oxidative iodination of some aromatic amines, either under microwave irradiation or conventional heating, is reported, using diiodine and ortho-periodic acid as the oxidant. The reactions were carried out in boiling CH2Cl2 solutions under a reflux condenser. For the microwave assisted reactions, the reaction times were always notably shortened, but the yields were usually less influenced as compared with the conventional method.
- Sosnowski, Maciej,Skulski, Lech,Wolowik, Katarzyna
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Read Online
- Iodination of activated aromatic compounds using nanostructure solid acid catalyst
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Nanoporous silica anchored with sulfonic acid groups effectively catalyzes the iodination of aromatic compounds. The reaction was performed in water using hydrogen peroxide as oxidant. The recyclability of catalyst in green media significantly contributes to the environmental friendliness of the procedure.
- Hosseini, Abolfazl,Khalilzadeh, Mohammad A.,Keipour, Hoda,Tajbakhsh, Mahmood
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Read Online
- NCBSI/KI: A Reagent System for Iodination of Aromatics through in Situ Generation of I-Cl
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In situ iodine monochloride (I-Cl) generation followed by iodination of aromatics using NCBSI/KI system has been developed. The NCBSI reagent requires no activation due to longer bond length, lower bond dissociation energy, and higher absolute charge density on nitrogen. The system is adequate for mono- and diiodination of a wide range of moderate to highly activated arenes with good yield and purity. Moreover, the precursor N-(benzenesulfonyl)benzenesulfonamide can be recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.
- Palav, Amey,Misal, Balu,Chaturbhuj, Ganesh
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p. 12467 - 12474
(2021/08/24)
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- Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes
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Owing to both Lewis and Bronsted acid active sites on sulfated polyborate under homogenous conditions, we were keen on developing iodination protocol of arenes that can meet the requirement of regioselectivity and higher yield. The sulfated polyborate activates N-iodosuccinimide for mono iodination of highly activated substrates viz. phenols, anilines under anhydrous condition. Water tunes sulfated polyborate to generate more Bronsted acid sites resulting in rapid activation of NIS for diiodination. The protocol was equally applicable to diiodination of 4-hydroxyphenylacetic acid to synthesize 4-hydroxy-3,5-diiodophenylacetic acid, an intermediate of tiratricol, a thyroid treatment drug. This protocol was further integrated via one-pot sequential iodination and Sonogashira coupling to synthesize aryl acetylenes, building blocks for the synthesis of a variety of specialty chemicals, API, and natural products.
- Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
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supporting information
(2021/05/26)
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- Preparation method of 2-bromo-5-iodo-benzyl alcohol
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The invention relates to the technical field of organic synthesis, and discloses a preparation method of 2-bromine-5-iodine-benzyl alcohol, which comprises the following steps: S1, o-benzylamine, a phase transfer catalyst, ammonium bicarbonate and an iodination reagent are subjected to iodination reaction to generate 2-methyl-4-iodoaniline; S2, the 2-methyl-4-iodoaniline is subjected to a diazotization reaction and a bromination reaction, and 2-bromine-4-iodobenzene is generated; S3, the 2-bromine-4-iodobenzene reacts with an initiator and N-bromosuccinimide, so as to generate 2-bromine-4-iodobromomethyl benzene; and S4, the 2-bromine-4-iodine bromomethyl benzene reacts with alkali, so as to generate the 2-bromine-5-iodine-benzyl alcohol. The preparation method disclosed by the invention is simple in process operation, few in three wastes and beneficial to industrial production; and no isomer is generated in the iodinated product, reduction of lithium aluminum hydride is not needed, and the problem of high operation risk caused by a large amount of hydrogen generated during reduction of lithium aluminum hydride can be effectively avoided.
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Paragraph 0038-0040
(2021/08/11)
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- A novel DMSO-assisted regioselective iodination of aniline analogues
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A metal- and oxidant-free electrophilic iodination of aniline analogues was achieved in high to excellent yields at room temperature in MTBE with 0 or 3.5 equivalents of DMSO. Examined substituents include N-alkyl, N,N-dialkyl, N-morpholinyl and N-piperazinyl as well as methyl, Br, CN and CO2CH3 aryl ring substitutions.
- Bovonsombat, Pakorn,Lorpaiboon, Wanutcha,Laoboonchai, Sarocha,Sriprachaya-anunt, Prima,Yimkosol, Warangkana,Siriphatcharachaikul, Natthapatch,Siricharoensang, Pornpawit,Kangwannarakul, Terawee,Maeda, Jin,Losuwanakul, Satreerat,Mahesh Abhyankar, Maitraye
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- Sodium sulfate-hydrogen peroxide-sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones
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The regioselective bromination and iodination of unprotected aromatic primary amines using enclathrated hydrogen peroxide as an oxidant under mild conditions has been developed, in which potassium bromide (KBr) and potassium iodide (KI) were used as brominating and iodinating agents, respectively. The adduct shows not only regioselectivity for para- or ortho-isomers but also a remarkable chemoselectivity for monobromination. Selective oxidation of sulfides to sulfoxides and sulfones has also been studied and good to excellent yields of the desired products were obtained. Acetic acid was found to be the solvent of choice for these reactions. This simple method represents an ecologically benign and alternative pathway for the oxidative halogenation of anilines and the oxidation of sulfides to sulfoxides and sulfones.
- Gayakwad, Eknath M.,Patel, Khushbu P.,Shankarling, Ganapati S.
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supporting information
p. 6001 - 6009
(2019/04/17)
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- Indole and quinoline derivatives and its preparation method and application
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The invention provides an indoloquinoline derivative, a preparation method and application thereof in preparing antitumor drugs and antiviral drugs. The chemical structure of the indoloquinoline derivative is shown as a formula I. Experiments show that a partly-boric-acid-modified indoloquinoline derivative and a non-boric-acid-modified indoloquinoline derivative have strong inhibition effect on various tumor cell strains, thereby being capable of being used for preparation of the antitumor drugs, and have strong antiviral activity, thereby being capable of being used for preparation of the antiviral drugs.
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Paragraph 0068; 0069
(2017/02/28)
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- Regioselective iodination of aryl amines using 1,4-dibenzyl-1,4-diazoniabicyclo [2.2.2] octane dichloroiodate in solution and under solvent-free conditions
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1,4-Dibenzyl-1,4-diazoniabicyclo[2.2.2]octane dichloroiodate is an efficient and regioselective reagent for iodination of aryl amines. A wide variety of aryl amines in reaction with this reagent afforded regioselectively iodinated products. The iodination reaction can be carried out in solution or under solvent-free condition at room temperature.
- Alikarami, Mohammad,Nazarzadeh, Somayeh,Soleiman-Beigi, Mohammad
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p. 157 - 162
(2015/01/30)
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- High birefringence bistolane liquid crystals: Synthesis and properties
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Twenty liquid crystals both symmetrical and non-symmetrical bistolanes with terminal alkyl, alkoxy and alkylsulfanyl chain and lateral methyl or ethyl group have been synthesized via Sonogashira cross-coupling and their mesomorphic properties have been studied. Most compounds exhibit an enantiotropic nematic phase in a broad temperature range (>40 °C). Optical properties of selected compounds have been investigated. They exhibit a high value of birefringence (>0.4).
- W?g?owska, Dorota,Kula, Przemys?aw,Herman, Jakub
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p. 403 - 408
(2016/01/09)
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- Photo-induced Metal-Catalyst-Free Aromatic Finkelstein Reaction
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The facile iodination of aromatic compounds under mild conditions is a great challenge for both organic and medicinal chemistry. Particularly, the synthesis of functionalized aryl iodides by light has long been considered impossible due to their photo-lability, which actually makes aryl iodides popular starting materials in many photo-substitution reactions. Herein, a photo-induced halogen exchange in aryl or vinyl halides has been discovered for the first time. A broad scope of aryl iodides can be prepared in high yields at room temperature under exceptionally mild conditions without any metal or photo-redox catalysts. The presence of a catalytic amount of elemental iodine could promote the reaction significantly.
- Li, Lu,Liu, Wenbo,Zeng, Huiying,Mu, Xiaoyue,Cosa, Gonzalo,Mi, Zetian,Li, Chao-Jun
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supporting information
p. 8328 - 8331
(2015/07/15)
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- Largely blue-shifted emission through minor structural modifications: Molecular design, synthesis, aggregation-induced emission and deep-blue OLED application
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By simply introducing additional groups with different size and conjugation degree to the 2,2′-positions of BTPE, four BTPE derivatives are prepared which give blue or deep-blue EL emissions when used as emitters in non-doped OLEDs, as the result of the tuned dihedral angles of the biphenyl cores (up to ~89°), providing a new approach to design AIE luminogens with blue and deep-blue emissions. The Royal Society of Chemistry.
- Huang, Jing,Sun, Ning,Chen, Pengyu,Tang, Runli,Li, Qianqian,Ma, Dongge,Li, Zhen
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supporting information
p. 2136 - 2138
(2014/02/14)
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- Cheap and easy synthesis of highly functionalized (het)aryl iodides via the aromatic finkelstein reaction
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Aryl iodides are superior coupling partners in cross-couplingA- reactions compared to the corresponding chlorides or bromides. Unfortunately, the iodides are much more expensive, if commercially available at all, than the other halides. Thus, it is often mandatory to transform the available bromides into the corresponding iodides. The copper-catalyzed aromatic Finkelstein reaction turned out to be the method of choice to prepare a number of highly functionalized iodo(het)aryls, including pyridines, 2,2′-bipyridines, and chiral compounds. Georg Thieme Verlag Stuttgart? New York.
- Meyer-Eppler, Georg,Kuechler, Lea,Tenten, Christina,Benkhaeuser, Christian,Brueck, Stefanie,Luetzen, Arne
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p. 1085 - 1090
(2014/05/06)
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- Ionic liquid iodinating reagent for mild and efficient iodination of aromatic and heteroaromatic amines and terminal alkynes
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Hexamethylene bis(N-methylimidazolium) bis(dichloroiodate) (HMBMIBDCI), an ionic liquid iodinating reagent, have been prepared and characterized. Its ability to perform iodination reactions with a variety of substrates has been explored. In general, iodination reactions of aromatic and heteroaromatic amines proceed with good yields in the absence of solvent. Reactions of terminal alkynes in the presence of 1,8-diazabicyclo [5.4.O] undec-7-ene and tetrahydrofuran have been investigated as well.
- Nouzarian, Mahboobe,Hosseinzadeh, Rahman,Golchoubian, Hamid
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supporting information
p. 2913 - 2925
(2013/09/02)
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- Regioselective bromination and iodination of aromatic substrates promoted by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane
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Selective and efficient bromination and iodination of aromatic compounds by ammonium bromide and ammonium iodide, respectively, under promotion of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane have been explored. Mild reaction conditions, high selectivity and yield, and high reaction rate are some of the major advantages of this synthetic method.
- Azarifar, Davood,Khosravi, Kaveh,Najminejad, Zohreh,Soleimani, Khadijeh
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experimental part
p. 321 - 326
(2012/08/14)
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- Remarkable switch in the regiochemistry of the iodination of anilines by N-iodosuccinimide: Synthesis of 1,2-dichloro-3,4-diiodobenzene
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Direct iodination of anilines by NIS in polar solvents (such as DMSO) affords p-iodinated products with up to >99% regioselectivity. Switching to less polar solvents (such as benzene) in the presence of AcOH inverts this outcome toward dramatically increased or preferential generation of the o-isomers, also with up to >99% regioselectivity. This finding was exploited in the synthesis of 1,2-dichloro-3,4-diiodobenzene. Georg Thieme Verlag Stuttgart - New York.
- Shen, Hao,Vollhardt, K. Peter C.
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supporting information; experimental part
p. 208 - 214
(2012/03/11)
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- P-Iodinations in hydrocarbon media: Continuous flow reactor application
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Regiospecific iodination of aryl amines, that is, aryl compounds possessing strong electron donating groups (EDG's) in the p-position, is described. This procedure features not only the unique use of hydrocarbon media for such substitutions but also the absence of any oxidants aside from iodine itself. Further potential of this hydrocarbon media based electrophilic aromatic substitution is demonstrated by the coupling of the iodination with an in situ halogen/lithium exchange and product forming nucleophilic addition in a batch process. The protocol was ultimately scaled to a continuous flow reactor using an isolated p-iodoarylamine. Constituted as described, these procedures possess enhanced atom-economical, green and safety aspects compared to existing literature protocols.
- Slocum,Tekin, Kristen C.,Nguyen, Quang,Whitley, Paul E.,Reinscheld, Thomas K.,Fouzia, Begum
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experimental part
p. 7141 - 7145
(2012/01/05)
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- Regiospecific oxyhalogenation of aromatics over SBA-15-supported nanoparticle group IV-VI metal oxides
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TiOx, VOx, MoOx and WOx supported on SBA-15 exhibit efficient catalytic activity for oxyhalogenation of aromatics with the H2O2-halide ion system. Unlike the hitherto known solid catalysts, these reusable catalysts yield the para-halogenated product with 100% selectivity at 298 K and moderate acidic pH (3-5). The catalytic activity was enhanced by five orders of magnitude when supported on SBA-15. Springer Science+Business Media, LLC 2010.
- Saikia,Rajesh,Srinivas,Ratnasamy
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scheme or table
p. 190 - 201
(2010/11/05)
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- Iodination of aromatic compounds using potassium iodide and hydrogen peroxide
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A simple, efficient, regioselective, and ecofriendly method for oxyiodination of aromatic compounds is presented. In this method, the electrophilic substitutions of iodine generated in situ from KI as an iodine source and hydrogen peroxide as an oxygen source have been employed without any catalyst/mineral acid for the first time. Copyright Taylor & Francis Group, LLC.
- Reddy, K. Suresh Kumar,Narender,Rohitha,Kulkarni
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experimental part
p. 3894 - 3902
(2009/04/04)
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- Eco-friendly oxyiodination of aromatic compounds using ammonium iodide and hydrogen peroxide
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A new eco-friendly procedure for the oxyiodination of aromatic compounds with NH4I as an iodine source and H2O2 as an oxidant without any catalyst is presented.
- Narender,Reddy, K. Suresh Kumar,Mohan, K.V.V. Krishna,Kulkarni
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p. 6124 - 6128
(2008/03/12)
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- Eco-friendly oxidative iodination of various arenes with sodium percarbonate as the oxidant http://www.mdpi.org
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Six easy laboratory procedures are presented for the oxidative iodination of various aromatics, mostly arenes, with either molecular iodine or potassium iodide (used as the sources of iodinating species, I+ or I 3+), in the presence of sodium percarbonate (SPC), a stable, cheap, easy to handle, and eco-friendly commercial oxidant.
- Zielinska, Agnieszka,Skulski, Lech
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p. 1307 - 1317
(2007/10/03)
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- Eco-friendly Oxidative Iodination of Various Arenes with a Urea-Hydrogen Peroxide Adduct (UHP) as the Oxidant
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Three easy eco-friendly laboratory procedures are presented for the oxidative iodination of various activated and deactivated arenes with molecular iodine, in the presence of UHP (percarbamide), a stable, strongly H-bonded, solid urea-hydrogen peroxide adduct as the oxidant.
- Lulinski, Piotr,Kryska, Anna,Sosnowski, Maciej,Skulski, Lech
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p. 441 - 445
(2007/10/03)
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- Benzenesulfonamide derivatives and their use as MEK inhibitors
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Benzenesulfonamides of formula (I), in which W is OR1, NR2OR1, NRARB, NR2NRARB, or NR2(CH2)2-4NRARBand the other variables as defined in the claims, are inhibitors of MEK and are effective in the treatment of proliferative diseases, cancer, stroke, heart failure, xenograft rejection, arthritis, cystic fibrosis, hepatomegaly, cardiomegaly, Alzheimer's disease, complications of diabetes, septic shock, and viral infection.
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- Iodination with Potassium Permanganate/Hydroiodic Acid/Acetonitrile Reagent
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Iodination of various aromatic amines proceeds smoothly with a preformed homogeneous mixture of hydroiodic acid potassium permanganate in acetonitrile. para-Substituted products were obtained in high yields (71-78%) within twelve hours at room temperature. With a slight modification of the permanganate, hydroiodic acid and substrate ratio, iodination of alkynes to vic-diiodoalkenes can be carried out at 60 °C in 65-87% yield.
- Chen, Jyh-An,Lin, Ching-Shan,Liu, Lilian Kao
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- Halogenation Using Quaternary Ammonium Polyhalides. VII. Iodination of Aromatic Amines by Use of Benzyltrimethylammonium Dichloroiodate(1-)
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The reaction of aromatic amines with benzyltrimethylammonium dichloroiodate(1-) in dichloromethane-methanol in the presence of calcium carbonate powder for several hours at room temperature gave selectively iodo-substituted aromatic amines in good yields.
- Kajigaeshi, Shoji,Kakinami, Takaaki,Yamasaki, Hiromichi,Fujisaki, Shizuo,Okamoto, Tsuyoshi
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p. 600 - 602
(2007/10/02)
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- Electrophilic Aromatic Substitution Reactions: Part III - Iodination of Anilines with Iodine Monochloride in Presence and Absence of a Surfactant
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Rates of iodination of aniline and substituted anilines with iodine monochloride have been measured in 30percent(v/v) aqueous methanol, isopropanol and dimethylformamide.The effects of perchloric acid, sodium chloride and surfactant (NaLS) have been investigated.Effect of dielectric constant on rates has also been tested.The Hammett ρ(+) values have been measured in 30percent(v/v) methanol-H2O, isopropanol-H2O and dimethylformamide-H2O mixtures in the presence an absence of sodium lauryl sulphate.The Hammett ρ(+) values range from -6.82 to -6.00.These results confirm Wheland type of transition state.The activation parameters are consistent with the proposed mechanism.
- Shashidhar, G. V. S.,Satyanarayana, N.,Sundaram, E. V.
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p. 333 - 335
(2007/10/02)
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