- Salicylaldimine-functionalized poly(m-phenyleneethynylene) as turn-on chemosensor for ferric ion
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A new turn on fluorescent probe for ferric ion based on poly(m-phenyleneethynylene salicylaldimine) (PPE-IM) has been developed. The preparation of PPE-IM involves post-polymerization functionalization of the corresponding polymeric amine, PPE-AM, via the condensation with salicylaldehyde. The degree of polymerization of both PPE-IM and PPE-IM is 17 with polydispersity index of 1.5. In aqueous solution, the polymeric PPE-IM is highly stable unlike its small molecule analog which is gradually hydrolyzed. The weak fluorescence of initial PPE-IM (λem = 470) is greatly enhanced by 300 folds upon the addition of Fe3+. The 1H NMR reveals that the fluorescence enhancement is caused by Fe3+-induced hydrolysis of the imine group. The sensing system shows a detection limit of 0.14 μM of Fe3+.
- Thavornsin, Nopparat,Rashatasakhon, Paitoon,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
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Read Online
- AN IMPROVED ONE POT, ONE STEP PROCESS FOR THE HALOGENATION OF AROMATICS USING SOLID ACID CATALYSTS
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The present invention disclosed an improved one pot, one step process for halogenation of compound of formula (II) to afford corresponding halogenated compound of formula (I) having improved yield and increased selectivity under very mild conditions.
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Page/Page column 0047; 0048
(2019/04/18)
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- Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst
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The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.
- Murray, James I.,Flodén, Nils J.,Bauer, Adriano,Fessner, Nico D.,Dunklemann, Daniel L.,Bob-Egbe, Opetoritse,Rzepa, Henry S.,Bürgi, Thomas,Richardson, Jeffery,Spivey, Alan C.
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supporting information
p. 5760 - 5764
(2017/05/12)
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- NOVEL RECYCLABLE IODINATING AGENT AND ITS APPLICATIONS
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The present invention provides a novel recyclable catalysts of formula A, [Formula A should be inserted here] wherein X is selected from the group consisting of [Formula should be inserted here] The present invention also provides a novel recyclable iodinating agent of formula I, II or III and a process for the synthesis thereof. [ Formula I, II & III should be inserted here] Further, the present invention provides a process of halogenation of amines and heterocyclic compounds by employing recyclable catalyst of formula (I).
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Page/Page column 16
(2016/11/07)
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- Iodination of industrially important aromatic compounds with aqueous potassium triiodide
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A new reagent system consisting of aqueous KI3in AcOH and NaIO4as oxidant has been found to be effective in iodinating a variety of commercially important aromatic substrates under ambient conditions. The presence of Na2SO3enhances the yield and the product purity. The procedure ensures high yields (72–98%) at room temperature in a short reaction time. A remarkable feature of this system is that even acidsensitive functionalities like anilines can be iodinated quantitatively.
- Sharma,Srivastava,Agarwal,Diwedi
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p. 433 - 436
(2016/06/13)
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- Recyclable ionic liquid iodinating reagent for solvent free, regioselective iodination of activated aromatic and heteroaromatic amines
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This article describes a simple, efficient method for iodination of activated aromatic and heteroaromatic amines using recyclable 1-butyl-3-methylpyridinium dichloroiodate (BMPDCI) as an ionic liquid iodinating reagent, in the absence of any solvent. The main advantages are a simple efficient procedure, good yields and no need for any base/toxic heavy metals, or oxidizing agents. The ionic liquid was recovered and recycled in five subsequent reactions, without much loss of activity. This method was applied for the synthesis of the antiprotozoal drug iodoquinol and the antifungal drug clioquinol.
- Deshmukh, Amarsinh,Gore, Babasaheb,Thulasiram, Hirekodathakallu V.,Swamy, Vincent P.
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p. 88311 - 88315
(2015/11/09)
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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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- Highly Regioselective Iodination of Arenes via Iron(III)-Catalyzed Activation of N-Iodosuccinimide
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An iron(III)-catalyzed method for the rapid and highly regioselective iodination of arenes has been developed. Use of the powerful Lewis acid, iron(III) triflimide, generated in situ from iron(III) chloride and a readily available triflimide-based ionic liquid allowed activation of N-iodosuccinimide (NIS) and efficient iodination under mild conditions of a wide range of substrates including biologically active compounds and molecular imaging agents.
- Racys, Daugirdas T.,Warrilow, Catherine E.,Pimlott, Sally L.,Sutherland, Andrew
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supporting information
p. 4782 - 4785
(2015/10/12)
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- Greener iodination of arenes using sulphated ceria-zirconia catalysts in polyethylene glycol
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An environmentally benign method for the selective monoiodination of diverse aromatic compounds has been developed using reusable sulphated ceria-zirconia under mild conditions. The protocol provides moderate to good yields and selectively introduces iodine at the para/ortho position in monosubstituted arenes. SO42-/Ce0.07Zr 0.93O2 was found to be the best choice for the synthesis of aryl iodides in high yield, presumably due to the maximum number of acid sites (4.23 mmol g-1) among the various compositions of the catalyst system.
- Kahandal, Sandeep S.,Kale, Sandip R.,Gawande, Manoj B.,Zboril, Radek,Varma, Rajender S.,Jayaram, Radha V.
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p. 6267 - 6274
(2014/01/23)
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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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p. 2913 - 2925
(2013/09/02)
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- Harnessing reversible oxidative addition: Application of diiodinated aromatic compounds in the carboiodination process
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An I for an I: Conditions for the intramolecular carboiodination and the simultaneous convergent intramolecular carboiodination/intermolecular Heck reaction of various diiodoarenes were developed. The ability of the Pd 0/QPhos catalyst/ligand combination to undergo reversible oxidative addition allows these reactions to proceed well, thus increasing both the appeal and utility of this class of substrates in site-selective cross-coupling reactions. Copyright
- Petrone, David A.,Lischka, Matthias,Lautens, Mark
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supporting information
p. 10635 - 10638
(2013/10/21)
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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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- Ecofriendly iodination of activated aromatics and coumarins using potassium iodide and ammonium peroxodisulfate
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An environmentally benign protocol for the iodination of activated aromatics, such as phenols, anilines, and hydroxycou-marins, using inexpensive commercially available potassium iodide and ammonium peroxodisulfate (1:2.5 molar equivalents per mole of substrate) in aqueous methanol (MeOH-H 2O, 6:1) at room temperature has been developed. The protocol provides for ortho-selective monoiodination as the predominant product without added acid and it is compatible with a number of common oxidizible functional groups, such as formyl, benzylic C-H, aromatic amines and hydroxymethyl. Good to acceptable yields of monoiodinated products in acceptable reaction times and exclusive ortho-iodination for 7-hydroxycoumarins, despite the presence of vinylogous electronrich C3, are some of the key advantageous features of the method. Georg Thieme Verlag Stuttgart.
- Ganguly, Nemai C.,Barik, Sujoy Kumar,Dutta, Sanjoy
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experimental part
p. 1467 - 1472
(2010/09/16)
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- Mild and efficient iodination of aromatic and heterocyclic compounds with the NaClO2/NaI/HCl system
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NaClO2/NaI in the presence of HCl is a mild, cheap, and non-toxic reagent for the iodination of phenols, including estradiol and naphthol, aromatic amines, and heterocyclic substrates, e.g., indoles, 8-hydroxyquinoline, imidazole, in fair to excellent yields by a very simple isolation protocol. The scope of the procedure is exemplified by the first iodination of 5-nitroindole to 3-iodo-5-nitroindole in 75% yield.
- Lista, Liliana,Pezzella, Alessandro,Napolitano, Alessandra,d'Ischia, Marco
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p. 234 - 239
(2008/09/16)
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- Convenient and efficient method for the iodination of aromatic amines by pyridinium iodochloride
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A simple and efficient method for the iodination of aromatic amines using pyridinium iodochloride (PyICl) in methanol as solvent is reported. Mild reaction conditions, short reaction time, and good to excellent yields of the product are the noteworthy advantages of the method. Pyridinium iodochloride is an efficient solid iodinating reagent and can be handled safely. Copyright Taylor & Francis Group, LLC.
- Khansole, Sandeep V.,Junne, Subhash B.,Sayyed, Mudassar A.,Vibhute, Yeshwant B.
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p. 1792 - 1798
(2008/09/20)
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- LEWIS ACID CATALYZED HALOGENATION OF ACTIVATED CARBON ATOMS
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A practical and efficient method for halogenation of activated carbon atoms using readily available /V-haloimides and a Lewis acid catalyst has been disclosed. This methodology is applicable to a range of compounds and any halogen atom can be directly introduced to the substrate. The mild reaction conditions, easy workup procedure and simple operation make this method valuable from both an environmental and preparative point of view.
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Page/Page column 26
(2008/06/13)
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- Catalysis and regioselectivity of the aqueous Heck reaction by Pd(0) nanoparticles under ultrasonic irradiation
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An aqueous Heck reaction carried out under ultrasonic irradiation at the ambient temperature (25 °C) has been shown in this study to afford high yields of corresponding products. It was found that as a catalyst for the reaction palladium forms nanoparticles in-situ, characterized by transmission electron microscopy (TEM) and X-ray powder diffraction (XRD) analyses, and can be recycled. Furthermore, the Heck reaction under such mild and environmentally friendly conditions offers excellent regioselectivity of para-over ortho-substitution in phenyl iodides especially with electron-donating groups.
- Zhang, Zuhui,Zha, Zhenggen,Gan, Changsheng,Pan, Chongfeng,Zhou, Yuqing,Wang, Zhiyong,Zhou, Ming-Ming
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p. 4339 - 4342
(2007/10/03)
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- Acetonitrile-mediated synthesis of 2,4-dichloroquinoline from 2-ethynylaniline and 2,4-dichloroquinazoline from anthranilonitrile
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2,4-Dichloroquinolines and 2,4-dichloroquinazolines were synthesized from 2-ethynylanilines and anthranilonitriles, respectively, using diphosgene in acetonitrile and heating at 130 °C or 150 °C for 12 hours. This reaction was applied to the synthesis of 4,6-dichloropyrazolo[3,4-d]pyrimidine (dichloro-9H-isopurine). The postulated mechanism is also described. Georg Thieme Verlag Stuttgart.
- Lee, Jae Hak,Lee, Byoung Se,Shin, Hyunik,Nam, Do Hyun,Chi, Dae Yoon
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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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- Synthesis of diiodo- and triiodoanilines by iodination of aniline with potassium dichloroiodate and preparation of 1,3,5-triiodobenzene
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A new chemoselective procedure was developed for the synthesis of 2,4,6-triiodoaniline and 2,4-diiodoaniline by the reaction of aniline with potassium dichloroiodate in dilute HCl. Subsequent deamination of 2,4,6-triiodoaniline afforded 1,3,5-triiodobenzene in good yield.
- Vatsadze,Titanyuk,Chernikov,Zyk
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p. 471 - 473
(2007/10/03)
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- Experimental and theoretical investigation of the coarctate cyclization of (2-ethynylphenyl)phenyldiazenes
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A new route to substituted 2-phenyl-2H-indazoles through the cyclization of (2-ethynylphenyl)-phenyldiazenes is presented. A coarctate reaction pathway forms the isoindazole carbene under neutral conditions, at moderate temperatures, and without the requirement of a carbene stabilizer. A wide variety of previously unknown diazene precursors was synthesized and cyclized. Trapping of the carbene with a silyl alcohol followed by deprotection affords the 3-hydroxymethyl-2-phenyl-2H-indazoles in good overall yield. The free carbene could also be trapped as a [2 + 1] cycloadduct with 2,3-dimethyl-2- butene.
- Shirtcliff, Laura D.,Weakley, Timothy J. R.,Haley, Michael M.,Koehler, Felix,Herges, Rainer
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p. 6979 - 6985
(2007/10/03)
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- 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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p. 867 - 870
(2007/10/03)
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- Aromatic iodination with the I2-HgX2 combination
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The reaction of differnt aromatic compounds 1a-1t with iodine and a mercury(II)-salt 2 [mercury(II) chloride, nitrate or triflate] (1:1:1 molar ratio) in dichloromethane at room temperature leads to the corresponding iodoarene 3, the obtained regiochemistry being the expected. Concerning the mercury(II) salt, the observed reactivity decreased in the series triflate > nitrate > chloride according to their ionic character. An activation of the iodine molecule by the mercury(II) salt followed by a S(E) reaction with the aromatic compounds is postulated as the possible mechanism.
- Bachki, Abderrazak,Foubelo, Francisco,Yus, Miguel
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p. 5139 - 5146
(2007/10/02)
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- Photosensitised Reactions of Aniline
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The photosensitisation effect of some acetophenones, benzophenone and peonol alone or in combination with iodine or of iodine alone has been studied on the irradiation of aniline.While photosensitisation with a ketone yields only azobenzene, the sensitisation with ketone and iodine or iodine alone yields only iodoanilines but no azobenzene.The mechanistic aspects have been discussed.
- Anjaneyulu, A. S. R.,Mallavadhani, U. V.
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p. 154 - 155
(2007/10/02)
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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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