- Tolane-based bent bolaamphiphiles forming liquid crystalline hexagonal honeycombs with trigonal symmetry
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Bolaamphiphiles consisting of a bent 1,3-bis(phenylethynyl)benzene core with two terminal glycerol units, a lateral n-alkyl chain in the bay-position and a methyl group at the apex of the central 1,3-substituted benzene ring have been synthesized via Sono
- Gao, Hongfei,Cheng, Huifang,Liu, Qijing,Xiao, Yulong,Prehm, Marko,Cheng, Xiaohong,Tschierske, Carsten
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- Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols
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An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high yields. Gram-scale reactions, as well as the scope of this protocol, were explored with electron-rich and electron-poor phenols as well as heterocycles. Quantum chemistry calculations revealed PhII(OH)·NH3 to be the most plausible iodinating active species as a reactive "I+" synthon. In light of the relevance of the iodoarene moiety, we present herein a practical, efficient, and simple procedure with a broad functional group scope that allows access to the iodoarene core unit.
- Satkar, Yuvraj,Yera-Ledesma, Luisa F.,Mali, Narendra,Patil, Dipak,Segura-Quezada, Luis A.,Ramírez-Morales, Perla I.,Solorio-Alvarado, César R.,Navarro-Santos, Pedro
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p. 4149 - 4164
(2019/04/30)
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- Synthesis of Silylbiaryl Triflates by Chemoselective Suzuki Reaction
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A modular approach for the synthesis of functionalized silylbiaryl triflates has been developed. Iodinated silylaryl triflates were prepared via a gram-scale diiodination reaction, followed by a one-flask transformation, in 42-52% overall yield. The iodin
- Moreira, Bárbara V.,Muraca, Ana Carolina A.,Raminelli, Cristiano
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supporting information
p. 1093 - 1102
(2017/02/24)
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- Enhancing the synthetic utility of 3-haloaryne intermediates by their efficient Generation from readily synthesizable ortho-iodoaryl triflate-type precursors
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Generation of 3-haloarynes from o-iodoaryl triflate-type precursors is reported. The method enables the generation of 3-fluorobenzyne with significantly high electrophilicity at -78 °C, allowing the formation of a three-component-coupled product between 3
- Yoshida, Suguru,Nagai, Akira,Uchida, Keisuke,Hosoya, Takamitsu
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supporting information
p. 733 - 736
(2017/09/01)
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- Molybdenum and Tungsten Alkylidene Complexes That Contain a 2-Pyridyl-Substituted Phenoxide Ligand
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In the interest of preparing molybdenum and tungsten alkylidene complexes for olefin metathesis that are longer-lived at high temperatures (~150 °C or above), we synthesized complexes that contain a phenoxide ligand with a 2-pyridyl in one ortho position and a mesityl (Mes) or 2,4,6-i-Pr3C6H2 (Trip) in the other ortho position ([MesON]- or [TripON]-, respectively). The alkylidene (neophylidene) complexes that were prepared include W(O)(CHCMe2Ph)(Me2Pyr)(RON) (R = Mes or Trip), Mo(NC6F5)(CHCMe2Ph)(RON)Cl, Mo(N-2,6-Me2C6H3)(CHCMe2Ph)(RON)Cl, Mo(N-t-Bu)(CHCMe2Ph)(RON)Cl, and M(N-2,6-i-Pr2C6H3)(CHCMe2Ph)(TripON)(OTf) (M = Mo or W). The reaction between Mo(NAr)(CHCMe2Ph)(TripON)(OTf) and ethylene yielded an ethylene complex, Mo(NAr)(C2H4)(TripON)(OTf)(ether). All neophylidene complexes were essentially unreactive toward terminal olefins at 22 °C and showed modest homocoupling activity (at 80 or 100 °C) and alkane metathesis activity (at 150 and 200 °C). W(O)(CHCMe2Ph)(Me2Pyr)(MesON) also stereoselectively polymerized several substituted norbornadienes at 100 °C.
- Sues, Peter E.,John, Jeremy M.,Bukhryakov, Konstantin V.,Schrock, Richard R.,Müller, Peter
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supporting information
p. 3587 - 3593
(2016/11/06)
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- Ultrasound-promoted rapid and efficient iodination of aromatic and heteroaromatic compounds in the presence of iodine and hydrogen peroxide in water
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A rapid and efficient ultrasound-promoted protocol for iodination of aromatic and heteroaromatic compounds, using molecular iodine in the presence of aqueous hydrogen peroxide in water without any cosolvent, has produced versatile iodinated organic molecules with potential application in organic synthesis and medicine in short reaction times and good to excellent yields. Copyright
- Ferreira, Irlon M.,Casagrande, Gleison A.,Pizzuti, Lucas,Raminelli, Cristiano
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supporting information
p. 2094 - 2102
(2014/07/07)
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- One-pot synthesis of 2,2′-bisbenzofurans using cuprous chloride as a catalyst
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A variety of novel 5,5′-disubstituted-2,2′-bisbenzofuran derivatives were synthesized by treatment of 4-substituted-2-(2- trimethylsilylethynyl)phenyl tert-butyldimethylsilyl ether analogues with CuCl as a catalyst in 62-82% isolated yields. This novel st
- Pan, Wen-Bin,Chen, Chin-Chau,Wei, Li-Lan,Wei, Li-Mei,Wu, Ming-Jung
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p. 2655 - 2657
(2013/06/05)
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- Small-molecular, non-peptide, non-ATP-competitive polo-like kinase 1 (Plk1) inhibitors with a terphenyl skeleton
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Polo-like kinase (Plk) 1 is a serine-threonine protein kinase that plays a role in cell division, and its overexpression is highly correlated with aggressiveness and prognosis of many cancers. We have designed, synthesized and evaluated a series of terphe
- Mita, Yusuke,Noguchi-Yachide, Tomomi,Ishikawa, Minoru,Hashimoto, Yuichi
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p. 608 - 617
(2013/02/25)
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- Regiocomplementary cycloaddition reactions of boryl- and silylbenzynes with 1,3-dipoles: Selective synthesis of benzo-fused azole derivatives
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Benzo-fused nitrogen-containing heterocycles are abundant in biologically active compounds. One of the most important methods for preparing such heterocycles is the (3 + 2) cycloaddition reaction of benzynes with 1,3-dipolar compounds. However, the reacti
- Ikawa, Takashi,Takagi, Akira,Goto, Masahiko,Aoyama, Yuya,Ishikawa, Yoshinobu,Itoh, Yuji,Fujii, Satoshi,Tokiwa, Hiroaki,Akai, Shuji
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p. 2965 - 2983
(2013/06/26)
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- Gas-Chromatographic identifi cation of products formed in iodination of methyl phenols by retention indices
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Iodination reaction followed by conversion of iodine-substituted methylphenols to the corresponding trifl uoroacetates was suggested for improving the sensitivity of the gas-chromatographic determination of phenol and its methyl-substituted derivatives (al isomers of mono- and diethylphenols, 2,3,5-, 2,3,6-, and 3,4,5-trimethylphenols) in aqueous media. Acylation products of iodo methylphenols (104 compounds) were identifi ed by linear-logarithmic retention indices on a standard nonpolar polydimethylsiloxane stationary phase, and the pattern of their variation with the number and nature of substituents were characterized. A procedure for identifi cation of methyl-substituted phenols in water in their gas-chromatographic determination with an electron-capture detector was developed. Pleiades Publishing, Ltd., 2012.
- Gruzdev,Kuzivanov,Zenkevich,Kondratenok
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p. 1355 - 1365
(2013/01/15)
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- Iodination of anilines and phenols with 18-crown-6 supported ICl 2-
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A highly crystalline iodinating reagent, {[K·18-C-6]ICl 2}n, was synthesized in high yield (93%). The trihalide is supported by an 18-crown-6 macrocycle and forms a coordination polymer in the solid state. This reagent iodinates anilines and phenols efficiently under mild conditions. Controlled mono-iodination with anilines was easily achieved while poly-iodination was observed with phenols.
- Mbatia, Hannah W.,Ulloa, Olbelina A.,Kennedy, Daniel P.,Incarvito, Christopher D.,Burdette, Shawn C.
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experimental part
p. 2987 - 2991
(2011/06/16)
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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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- Peroxide/potassium iodide redox systems for in situ oxyiodination of organic compounds under liquid-phase and solvent-free conditions
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Iodination of certain aromatic amines and phenols are triggered by the oxidation of KI by peroxy compounds such as tert-butyl hydroperoxide ( tBuOOH) under liquid-phase and solvent-free conditions by grinding the reactants in a mortar with a pestle. The reactions afforded corresponding iodo derivatives in good yield with high regioselectivity (Table 1).
- Venkateshwarlu, Gattu,Premalatha, Akarapu,Chakradhar, Anuganti,Rajanna, Kamatala Chinna,Prakash, Pondichery Kuppuswamy Sai
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experimental part
p. 345 - 349
(2010/05/15)
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- Single bifunctional ruthenium catalyst for one-pot cyclization and hydration giving functionalized indoles and benzofurans
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Chemical equation Presented Bifunctional is more than twice as fun! At low loading, catalyst 1 (see scheme) can form two important heterocycle classes, apparently by attack of XH on a vinylidene intermediate. Aza- and nitroindoles can be formed, and all N-protecting groups tested (alkyl, allyl, sulfonyl) were tolerated. The newly formed ring can be deuterated in one step, and for substrates with two terminal alkynes, cyclization can be followed by hydration, making this catalyst uniquely versatile.
- Nair, Reji N.,Lee, Paul J.,Rheingold, Arnold L.,Grotjahn, Douglas B.
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supporting information; scheme or table
p. 7992 - 7995
(2010/09/18)
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- Preparation and regioselective Diels-Alder reactions of borylbenzynes: Synthesis of functionalized arylboronates
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(Figure Presented) B+ [4+2]: 3-Borylbenzynes undergo Diels-Alder reactions with substituted furans and pyrroles to give highly functionalized arylboronic acid derivatives with either good or exclusive regioselectivities (see picture). The effect of the boryl group on the regioselectivity arises from electronic rather than steric effects.
- Ikawa, Takashi,Takagi, Akira,Kurita, Yurio,Saito, Kozumo,Azechi, Kenji,Egi, Masahiro,Kakiguchi, Keisuke,Kita, Yasuyuki,Akai, Shuji
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supporting information; experimental part
p. 5563 - 5566
(2010/09/05)
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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 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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- Iodination of Thallium(I) salts of Phenols
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The iodination of thallium(I) salts of phenols is examined and the results are compared with those of the selective ortho-iodinating reagent thallium(I) acetate-iodine.
- Gambie, Richard C.,Larsen, David S.,Rutledge, Peter S.,Woodgate, Paul D.
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p. 767 - 769
(2007/10/03)
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- Synthesis of thyroxine: Biomimetic studies
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The biomimetic oxidative coupling of the ethyl ester of N-acetyl-3,5- diiodotyrosine (1) to yield the ethyl ester of N-acetylthyroxine (2) has been investigated. A putative mechanism involving phenolic coupling to yield an intermediate aryloxydienone (7) followed by an E2 elimination for loss of the side chain has been proposed. Oxidative couplings with analogous 4- substituted 3,5-diiodophenols indicate that a number of mechanisms are possible; these include quinone methide intermediates and S(N)2 substitutions in the intermediate aryloxydienones. Rearomatization of the intermediate aryloxydienones is a strong driving force for the loss of the side chains. The results indicate that 3,5-diiodo-4-aryloxydienones are good leaving groups in E2 and S(N)2 mechanisms. The synthetic method provides a facile synthesis of thyroxine analogues from readily available 4-substituted 3,5- diiodophenols. The biomimetic oxidative coupling of the ethyl ester of N-acetyl-3,5-diiodotyrosine (1) to yield the ethyl ester of N-acetylthyroxine (2) has been investigated. A putative mechanism involving phenolic coupling to yield an intermediate aryloxydienone (7) followed by an E2 elimination for loss of the side chain has been proposed. Oxidative couplings with analogous 4-substituted 3,5-diiodophenols indicate that a number of mechanisms are possible; these include quinone methide intermediates and SN2 substitutions in the intermediate aryloxydienones. Rearomatization of the intermediate aryloxydienones is a strong driving force for the loss of the side chains. The results indicate that 3,5-diiodo-4-aryloxydienones are good leaving groups in E2 and SN2 mechanisms. The synthetic method provides a facile synthesis of thyroxine analogues from readily available 4-substituted 3,5-diiodophenols.
- Bell, Natalie V.,Bowman, W. Russell,Coe, Paul F.,Turner, Andrew T.,Whybrow, Del
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p. 873 - 883
(2007/10/03)
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- Influence de la complexation sur la reactivite de nitrates d'halogenes
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Iodine nitrate or bromine nitrate in acetonitrile or in chloroform react with a variety of phenolic substrates to form both halogenated and nitrated products.In the presence of strong complexing agents of halonium ions, no reacting occurs, while in the presence of pyridine or triethylamine, only halogenated phenols exhibiting a strong ortho-directing effect of the phenolic function are produced. Keywords: phenols, iodine nitrate, bromine nitrate, halogenation, nitration.
- Gaude, Didier,Gellon, Gisele,Goaller, Raymond Le,Pierre, Jean-Louis
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p. 104 - 108
(2007/10/02)
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- Iodination of Phenols by Use of Benzyltrimethylammonium Dichloroiodate(1-)
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The reaction of phenols with benzyltrimethylammonium dichloroiodate(1-) in dichloromethane-methanol in the presence of CaCO3 or NaHCO3 for several hours at room temperature gave iodophenols in good yields.
- Kajigaeshi, Shoji,Kakinami, Takaaki,Yamasaki, Hiromichi,Fujisaki, Shizuo,Kondo, Manabu,Okamoto, Tsuyoshi
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p. 2109 - 2112
(2007/10/02)
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- IODINATION OF PHENOLS USING CHLORAMINE T AND SODIUM IODIDE
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A convenient procedure for the iodination of many substituted phenols uses chloramine T and sodium iodide in DMF, DMSO, or acetonitrile.
- Kometani, Tadashi,Watt, David S.,Ji, Tae
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p. 2043 - 2046
(2007/10/02)
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- Oxidation of Phenols with Iodine in Alkaline Methanol
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The use of iodine as an oxidizing agent for phenolic compounds has been explored.The reaction has been conducted in methanol containing such alkali as potassium hydroxide and, depending on the nature of the substituents and on the amount of iodine employed, leads to iodination, oxidation to give a stable phenoxy radical, oxidative dimerization, or benzylic oxidation.In general the reaction proceeds smoothly at room temperature, and under appropriate conditions yields of products are good to excellent.Oxidative dimerization of 2,4- and 2,6-di-tert-butylphenols invol-ves iodination followed by iodine-catalyzed dimerization.The oxidation of 4-methylphenols with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in methanol has been carried out for comparison.
- Omura, Kanji
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p. 3046 - 3050
(2007/10/02)
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