- Pd-Catalyzed Decarboxylative Ortho-Halogenation of Aryl Carboxylic Acids with Sodium Halide NaX Using Carboxyl as a Traceless Directing Group
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A highly regioselective Pd-catalyzed carboxyl directed decarboxylative ortho-C-H halogenation of cheap o-nitrobenzoic acids with NaX (X = I, Br) under aerobic conditions has been established. The utility of the method has been demonstrated by the gram-scale reaction and derivatization of the product. Experimental results have confirmed Pd and Bi played critical roles in the transformation and indicated the transformation might proceed via 2-halo-6-nitrobenzoic acid derivative intermediate.
- Fu, Zhengjiang,Jiang, Yongqing,Wang, Shuiliang,Song, Yuanyuan,Guo, Shengmei,Cai, Hu
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supporting information
p. 3003 - 3007
(2019/05/10)
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- Method for synthesizing m-iodonitrobenzene compound
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Provided is a method for synthesizing m-iodonitrobenzene; in the presence of oxygen gas, a palladium catalyst, a copper additive, a bismuth reagent and potassium phosphate, an o-nitrobenzoic acid compound and metal iodide are subjected to a substitution reaction in an organic solvent to form a corresponding m-iodonitrobenzene compound, wherein a metal in the metal iodide is an alkali metal or an alkaline earth metal. The method has obvious advantages of cheap and easily obtained reaction raw materials (including o-nitrobenzoic acid and MI), small amount of the metal catalyst, minimum environmental pollution with oxygen gas as an oxidant, good tolerance on various functional groups on an aromatic ring and the like. The method can be widely applied in the fields of synthesis of drugs, materials, natural products and the like in industrial and academic circles.
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Paragraph 0099-0100
(2018/03/24)
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- Transition-metal-free hydrogenation of aryl halides: From alcohol to aldehyde
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A transition-metal-and catalyst-free hydrogenation of aryl halides, promoted by bases with either aldehydes or alcohols, is described. One equivalent of benzaldehyde affords an equal yield as that of 0.5 equiv of benzyl alcohol. The kinetic study reveals that the initial rate of PhCHO is much faster than that of BnOH, in the ratio of nearly 4:1. The radical trapping experiments indicate the radical nature of this reaction. Based on the kinetic study, trapping and KIE experiments, and control experiments, a tentative mechanism is proposed. As a consequence, a wide range of (hetero)aryl iodides and bromides were efficiently reduced to their corresponding (hetero)arenes. Thus, for the first time, aldehydes are directly used as hydrogen source instead of other well-established alcohol-hydrogen sources.
- Zheng, Hong-Xing,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao
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supporting information
p. 5114 - 5117
(2017/11/07)
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- Gold(I)-catalyzed iodination of arenes
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A wide variety of electron-rich arenes were efficiently converted into the corresponding iodinated compounds via a gold(I)-catalyzed reaction under mild conditions. Georg Thieme Verlag Stuttgart. New York.
- Leboeuf, David,Ciesielski, Jennifer,Frontier, Alison J.
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supporting information
p. 399 - 402
(2014/03/21)
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- Synthesis and evaluation of diaryl sulfides and diaryl selenide compounds for antitubulin and cytotoxic activity
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We have devised a procedure for the synthesis of analogs of combretastatin A-4 (CA-4) containing sulfur and selenium atoms as spacer groups between the aromatic rings. CA-4 is well known for its potent activity as an inhibitor of tubulin polymerization, a
- Dos Santos, Edson Dos A.,Hamel, Ernest,Bai, Ruoli,Burnett, James C.,Tozatti, Camila Santos Suniga,Bogo, Danielle,Perdomo, Renata T.,Antunes, Alexandra M.M.,Marques, M. Matilde,Matos, Maria De F.C.,De Lima, Dênis P.
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supporting information
p. 4669 - 4673
(2013/08/23)
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- Negishi cross-coupling reaction as a route to isocombretastatins
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A series of isocombretastatins A has been synthesized by a new method based on the Negishi cross-coupling reaction in 19-84% yields. Five of the synthesized compounds exhibit high cytotoxic activity in nanomolar concentrations (IC50 = 1-100 n) towards Jurkat, K562, Colo357, and A549 cell lines. Georg Thieme Verlag Stuttgart · New York.
- Malysheva, Yulia B.,Buchvalova, Svetlana Y.,Svirshchevskaya, Elena V.,Fokin, Valery V.,Fedorov, Alexey Y.
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supporting information
p. 1772 - 1776
(2013/09/12)
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- Novel water-soluble anticancer agents derived from 4-arylcoumarins
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Novel 4-arylcoumarin derivatives were obtained. They are water-soluble analogs of the well-known anticancer drug combretastatin A-4. The key step of the synthesis involves the Suzuki-Miyaura cross-coupling. The water-soluble salts obtained exhibit conside
- Malysheva,Voitovich,Sharonova,Combes,Svirshchevskaya,Vodovozova,Fedorov
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p. 1103 - 1110
(2014/03/21)
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- New method of synthesis and biological evaluation of some combretastatin A-4 analogues
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A series of novel combretastatin A-4 analogues was synthesized in 36-64% yields by Negishi cross-coupling reaction under mild conditions. The prepared compounds exhibit good cytotoxicity against HBL100 epithelial cell lines (IC50=0.022-10.31 ). Georg Thieme Verlag Stuttgart · New York.
- Malysheva, Yulia B.,Combes, Sebastien,Fedorov, Alexey Yu.,Knochel, Paul,Gavryushin, Andrei E.
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supporting information; experimental part
p. 1205 - 1208
(2012/06/29)
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- Aromatic nitration under neutral conditions using N-bromosuccinimide/ silver(I) nitrate
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The use of N-bromosuccinimide and silver nitrate as a convenient reagent system for the nitration of aromatic compounds under neutral and environmentally safer reaction conditions is described.
- Nowrouzi, Najmeh,Mehranpour, Abdol Mohammad,Bashiri, Elham,Shayan, Zohre
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experimental part
p. 4841 - 4842
(2012/09/22)
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- Nitration of aromatic compounds under neutral conditions using the Ph 2PCl/I2/AgNO3 reagent system
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Aromatic compounds were nitrated efficiently under essentially neutral conditions by employing Ph2PCl in the presence of I2 and AgNO3. This method minimizes waste products compared to traditional methods and gives the corresponding mononitro derivatives in good to excellent yields in dichloromethane at room temperature.
- Nowrouzi, Najmeh,Zareh Jonaghani, Mohammad
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experimental part
p. 5081 - 5082
(2011/10/09)
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- Solvent-free iodination of arenes using iodine-silver nitrate combination
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A simple and environmentally safe general method of iodination of aromatic substrates under sovent-free conditions using the I2/AgNO3 combination in a solid state is reported. Both activated and deactivated aromatic compounds afford the respective aryl iodides in generally high yields (80-90%). Copyright Taylor & Francis Group, LLC.
- Yusubov, Mekhman S.,Tveryakova, Elena N.,Krasnokutskaya, Elena A.,Perederyna, Irina A.,Zhdankin, Viktor V.
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p. 1259 - 1265
(2008/02/01)
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- Oxidative iodination of deactivated arenes in concentrated sulfuric acid with I2/NaIO4 and KI/NaIO4 iodinating systems
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Deactivated arenes were mono- or diiodinated with strong electrophilic I+ reagents, which were prepared from NaIO4 and either I2 or KI in concentrated H2SO4 (minimum 95% by weight). In general a small excess of the dark brown iodinating solution was used (1.1/1.5 equivalents, for nitrobenzene two equivalents was required). The iodinations were conducted at 25-30 °C with a reaction time of 1-2 hours using either a 'direct' or an 'inverse' method of aromatic iodination to give mono- or diiodinated pure products in 31-91% optimized yields. Georg Thieme Verlag Stuttgart.
- Kraszkiewicz, Lukasz,Sosnowski, Maciej,Skulski, Lech
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p. 1195 - 1199
(2007/10/03)
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- Diphenylethylene compounds and uses thereof
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The present invention relates to Diphenylethylene Compounds and compositions comprising a Diphenylethylene Compound. The present invention also relates to methods for preventing or treating various diseases and disorders by administering to a subject in need thereof one or more Diphenylethylene Compounds. In particular, the invention relates to methods for preventing or treating cancer or an inflammatory disorder by administering to a subject in need thereof one or more Diphenylethylene Compounds. The present invention further relates to articles of manufacture and kits comprising one or more Diphenylethylene Compounds.
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- Easy, inexpensive and effective oxidative iodination of deactivated arenes in sulfuric acid
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Two 'model' deactivated arenes, benzoic acid and nitrobenzene, were effectively monoiodinated within 1 h at 25-30 °C, with strongly electrophilic I+ reagents, prior prepared from diiodine and various oxidants (CrO3, KMnO4, active MnO2, HIO 3, NaIO3, or NaIO4) in 90% (v/v) concd sulfuric acid (ca. 75 mol% H2SO4). Next, an I2/ NaIO3/90% (v/v) concd H2SO4 exemplary system was used to effectively mono- or diiodinate a number of deactivated arenes. All former papers dealing with the direct iodination of deactivated arenes are briefly reviewed.
- Kraszkiewicz, Lukasz,Sosnowski, MacIej,Skulski, Lech
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p. 9113 - 9119
(2007/10/03)
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- Convenient Nitration of Anisole and its Derivatives using an NO-O2 System
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Anisole and its derivatives are regioselectively nitrated by use of nitrogen monoxide-molecular dioxygen mixed gas under mild conditions.
- Mizuno, Kazuhiko,Tamai, Toshiyuki,Hashida, Isao,Otsuji, Yoshio,Inoue, Hiroo
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p. 284 - 285
(2007/10/03)
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- 13C NMR Spectra of Substituted o-Nitroanisoles and n-Butyl o-Nitrophenyl Ethers
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13C NMR analyses of substituted o-nitroanisoles and n-butyl o-nitrophenyl ethers are reported. Key Words: 13C NMR - o-Nitroanisoles - n-Butyl o-nitrophenyl ethers
- Zeegers, Petrus J.,Thompson, Malcolm J.
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p. 497 - 499
(2007/10/02)
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- A Novel Aromatic Iodination Method Using F2
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A new method for direct aromatic iodination with IF, made in situ from the corresponding elements, is described.Depending on the reaction time and temperature, mono- or polyiodination can be achieved.Even deactivated aromatic rings can be directly iodinated without the presence of any Friedel-Crafts catalyst.Sensitive groups such as aromatic aldehydes are not affected by the reagent.
- Rozen, Shlomo,Zamir, Dov
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p. 3552 - 3555
(2007/10/02)
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