- CuO nanoparticles: an efficient and recyclable catalyst for cross-coupling reactions of organic diselenides with aryl boronic acids
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We present here an efficient and ligand-free cross-coupling reaction of organic diselenides with aryl boronic acids using a catalytic amount of CuO nanoparticles in DMSO at 100 °C under air atmosphere. This is a general cross-coupling reaction and was performed with organic diselenides and aryl boronic acids bearing electron-withdrawing and electron-donating groups affording the corresponding selenides in good to excellent yields. The CuO nanoparticles can be easily recovered and utilized for further catalytic reactions.
- Alves, Diego,Santos, Cayane G.,Paix?o, Márcio W.,Soares, Letiére C.,Souza, Diego de,Rodrigues, Oscar E.D.,Braga, Ant?nio L.
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- Glycerol as a recyclable solvent for copper-catalyzed cross-coupling reactions of diaryl diselenides with aryl boronic acids
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We describe herein the use of glycerol as the solvent in the copper-catalyzed cross-coupling reaction of diaryl diselenides with arylboronic acids using CuI and DMSO as additive. This cross-coupling reaction was performed with diaryl diselenides and arylboronic acids bearing electron-withdrawing and electron-donating groups, affording the corresponding diaryl selenides in good to excellent yields. The glycerol-CuI mixture can be directly reused for further cross-coupling reactions.
- Ricordi, Vanessa G.,Freitas, Camilo S.,Perin, Gelson,Lenardao, Eder J.,Jacob, Raquel G.,Savegnago, Lucielli,Alves, Diego
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- Silver-Catalyzed Synthesis of Diaryl Selenides by Reaction of Diaryl Diselenides with Aryl Boronic Acids
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We described herein our results on the silver-catalyzed synthesis of diaryl selenides via a cross-coupling reaction of diaryl diselenides with aryl boronic acids. The methodology is tolerant to electron-donor and electron-withdrawing groups at the substrates and the desired products were obtained in good to excellent yields.
- Goldani, Bruna,Ricordi, Vanessa G.,Seus, Natália,Lenard?o, Eder J.,Schumacher, Ricardo F.,Alves, Diego
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- Magnesium-Induced Copper-Catalyzed Synthesis of Unsymmetrical Diaryl Chalcogenide Compounds from Aryl Iodide via Cleavage of the Se-Se or S-S Bond
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The methodology for a copper-catalyzed preparation of diaryl chalcogenide compounds from aryl iodides and diphenyl dichalcogenide molecules is reported. Unsymmetrical diaryl sulfide or diaryl selenide can be synthesized from aryl iodide and PhYYPh (Y = S, Se) with a copper catalyst (CuI or Cu2O) and magnesium metal in one pot. This reaction can be carried out under neutral conditions according to an addition of magnesium metal as the reductive reagent. Furthermore, it is efficiently available for two monophenylchalcogenide groups generated from diphenyl dichalcogenide.
- Taniguchi, Nobukazu,Onami, Tetsuo
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- Synthesis of diaryl selenides using electrophilic selenium species and nucleophilic boron reagents in ionic liquids
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We described herein the use of imidazolium ionic liquids [bmim]PF 6 and [bmim]BF4 in the selective, metal and catalyst-free synthesis of unsymmetrical diaryl selenides by electrophilic substitution in arylboron reagents with arylselenium halides (Cl and Br) at room temperature. This is a general substitution reaction and it was performed with arylboronic acids or potassium aryltrifluoroborates bearing electron-withdrawing or electron-donating groups, affording the corresponding diaryl selenides in good to excellent yields. The ionic liquid [bmim][PF6] was easily recovered and utilized for further substitution reactions.
- Freitas, Camilo S.,Barcellos, Angelita M.,Ricordi, Vanessa G.,Pena, Jesus M.,Perin, Gelson,Jacob, Raquel G.,Lenardao, Eder J.,Alves, Diego
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- Trichloroisocyanuric Acid-Promoted Synthesis of Arylselenides and Aryltellurides from Diorganyl Dichalcogenides and Arylboronic Acids at Ambient Temperature
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A transition-metal-free method for the synthesis of arylselenides and aryltellurides has been established based on the oxidative cross-coupling between diorganyl dichalcogenides and aryl boronic acids. With trichloroisocyanuric acid as an oxidant, the reaction proceeded smoothly to afford the desired products in 45–97% yields at ambient temperature. Three reaction reagents used in this method are stoichiometric and the oxidation by-product isocyanuric acid can be easily isolated and recovered. Besides of arylboronic acids, aryl trifluoroborates and aryl trihydroxyborates salts are also able to perform this transformation. (Figure presented.).
- Sun, Nan,Zheng, Kai,Sun, Pengyuan,Chen, Yang,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
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p. 3577 - 3584
(2021/06/15)
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- Photocatalyst-free photoredox synthesis of diaryl selenides by reaction of diselenides with aryldiazo sulfones
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A photcatalyst-free photoredox synthesis of diaryl selenides has been developed by coupling reaction of diselenides with aryldiazo sulfones. The reaction was accelerated under visible light irradiation without using a photocatalyst or photosensitizer. This approach facilitates the synthesis of diaryl selendes with a wide range of functional group tolerance.
- Jang, Jihoon,Kim, Rabin,Kim, Dae Young
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supporting information
p. 720 - 726
(2020/11/30)
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- Method for preparing asymmetric organic selenium ether compounds through metal-free chemical oxidation method (by machine translation)
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The method is mild in reaction condition, convenient to operate, high in 1 reaction condition, convenient 2 to operate, high in safety, wide in substrate range, high 2 - 8h in yield, particularly suitable for reaction of various poor 3 electric and sterically hindered arylboronic acid and diselenoxy ether, and capable of finishing most of the reaction 4h. (by machine translation)
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Paragraph 0059-0063
(2020/12/09)
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- Alternative Metal-Free Synthesis of Diorganoyl Selenides and Tellurides Mediated by Oxone
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We herein describe an alternative metal-free methodology for the synthesis of diorganyl selenides and tellurides mediated by Oxone . The products were obtained in moderate to excellent yields by reactions of diorganyl diselenides or ditellurides with aryl boronic acids mediated by Oxone with use of EtOH as the solvent. The methodology is applicable to a broad scope of diorganyl dichalcogenides and aryl boronic acids containing electron-rich, electron-poor, and sterically hindered substituents.
- Perin, Gelson,Duarte, Luis Fernando B.,Neto, José S. S.,Silva, Márcio S.,Alves, Diego
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supporting information
p. 1479 - 1484
(2018/05/03)
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- Composition for preventing or treating cancer comprising novel selenobenzene compound
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The present invention relates to a composition for preventing or treating cancer comprising, as an active ingredient, a novel selenobenzene compound represented by chemical formula 1. The selenobenzene compound according to the present invention inhibits
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Paragraph 0086; 0092-0098
(2018/06/20)
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- Asymmetric Heteroleptic Ir(III) Phosphorescent Complexes with Aromatic Selenide and Selenophene Groups: Synthesis and Photophysical, Electrochemical, and Electrophosphorescent Behaviors
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With the aim of evaluating the potential of selenium-containing groups in developing electroluminescent (EL) materials, a series of asymmetric heteroleptic Ir(III) phosphorescent complexes (Ir-Se0F, Ir-Se1F, Ir-Se2F, and Ir-Se3F) have been synthesized by using 2-selenophenylpyridine and one ppy-type (ppy = 2-phenylpyridine) ligand with a fluorinated selenide group. To the best of our knowledge, these complexes represent unprecedented examples of asymmetric heteroleptic Ir(III) phosphorescent emitters bearing selenium-containing groups. Natural transition orbital (NTO) analysis based on optimized geometries of the first triplet state (T1) have shown that the phosphorescent emissions of these Ir(III) complexes dominantly show 3π- π? features of the 2-selenophenylpyridine ligand with slight metal to ligand charge transfer (MLCT) contribution. In comparison with their symmetric parent complex Ir-Se with two 2-selenophenylpyridine ligands, these asymmetric heteroleptic Ir(III) phosphorescent complexes can show much higher phosphorescent quantum yields (φP) of ca. 0.90. Both the hole- and electron-trapping ability of these Ir(III) phosphorescent complexes can be enhanced by selenophene and fluorinated selenide groups to improve their EL efficiencies. The EL abilities of these asymmetric heteroleptic Ir(III) phosphorescent emitters fall in the order Ir-Se3F > Ir-Se2F > Ir-Se1F > Ir-Se0F. The highest EL efficiencies have been achieved by Ir-Se3F in the solution-processed OLEDs with external quantum efficiency (next), current efficiency (n L), and power efficiency (n P) of 19.9%, 65.6 cd A-1, and 57.3 lm W-1, respectively. These encouraging EL results clearly indicate the great potential of selenium-containing groups in developing high-performance Ir(III) phosphorescent emitters.
- Feng, Zhao,Wang, Dezhi,Yang, Xiaolong,Jin, Deyuan,Zhong, Daokun,Liu, Boao,Zhou, Guijiang,Ma, Miaofeng,Wu, Zhaoxin
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supporting information
p. 11027 - 11043
(2018/09/14)
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- Efficient heterogeneous copper-catalysed C–Se coupling of aryl iodides with symmetrical diselenides towards unsymmetrical monoselenides
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A highly efficient heterogeneous copper(I)-catalysed C–Se coupling of aryl iodides with diaryl diselenides was achieved in dimethylformamide at 110 °C under neutral conditions by using a 10 mol% of bipyridine-functionalised MCM-41-supported copper(I) complex [bpy-MCM-41-CuI] as the catalyst and magnesium as the reductive reagent, yielding a variety of unsymmetrical diaryl selenides in good to excellent yields. This heterogeneous copper catalyst can be easily recovered by a simple filtration of the reaction solution and recycled at least seven times without significant loss of activity.
- Zhao, Ruonan,Yan, Chenyu,Jiang, Yuanyuan,Cai, Mingzhong
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p. 584 - 588
(2018/11/27)
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- Atom-Economical Synthesis of Unsymmetrical Diaryl Selenides from Arylhydrazines and Diaryl Diselenides
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An atom-economical method for the synthesis of unsymmetrical diaryl selenides from arylhydrazines and stoichiometric amounts of diselenides was developed under mild conditions. The new and facile selenide synthesis involved the use of an inexpensive base in air to form unsymmetrical diaryl selenides in good yields. This C–Se radical arylation of diaryl diselenides was performed by forming aryl radicals from arylhydrazines under oxidative conditions. The formation of a phenyl radical was supported by trapping with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) in air. Therefore, this synthesis might involve a homolytic aromatic substitution (HAS) mechanism. The synthesis is both low costing and environmentally friendly and, therefore, may be useful for the practical synthesis of unsymmetrical diaryl selenides.
- Taniguchi, Toshihide,Murata, Akinori,Takeda, Motonori,Mizuno, Takumi,Nomoto, Akihiro,Ogawa, Akiya
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p. 4928 - 4934
(2017/09/13)
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- Iron(0) nanoparticles mediated direct conversion of aryl/heteroaryl amines to chalcogenides via in situ diazotization
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A simple procedure for the synthesis of organo-chalcogenides has been developed by the reaction of aryl/heteroaryl amines with di-aryl/heteroaryl dichalcogenides in the presence of tBuONO and Fe(0) nanoparticles. The reaction proceeds via in situ diazotization followed by chalcogenation. A series of functionalized diaryl/aryl heteroaryl/diheteroaryl/aryl-alkyl selenides, sulfides and tellurides have been obtained by this procedure. Significantly, using this procedure 2,4-dinitroaniline is converted to (2,4-dinitrophenyl)(phenyl)selane which is known as thioredoxin reductase (TR) and glutathione reductase (GR) inhibitor. The reaction goes by a radical pathway and a plausible mechanism has been suggested.
- Panja, Subir,Maity, Pintu,Kundu, Debasish,Ranu, Brindaban C.
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supporting information
p. 3441 - 3445
(2017/08/10)
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- METHOD OF PREPARING CORE-SHELL COPPER NANOPARTICLES IMMOBILIZED ON ACTIVATED CARBON AND METHOD OF PREPARING CHALCOGENIDE COMPOUND USING NANOPARTICLES AS CATALYST
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Disclosed herein is a method of preparing a Cu/Cu2O core-shell copper nanoparticle catalyst having high catalytic activity from [Cu3(BTC)2] and NaBH4 via a simple chemical reduction method. Also disclosed is a method of preparing a chalcogenide compound by using the nanoparticle catalyst as a heterogeneous catalyst in a cross-coupling reaction between a chalcogenide precursor compound and a boron-containing compound. The disclosed cross-coupling reaction is performed via a simple process, and the disclosed nanoparticle catalyst is compatible with various substrates under mild reaction conditions and exhibits excellent recyclability without a reduction in catalytic activity.
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Paragraph 0056; 0065
(2016/11/14)
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- Copper nanoparticles catalyzed Se(Te)-Se(Te) bond activation: A straightforward route towards unsymmetrical organochalcogenides from boronic acids
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A highly porous copper metal-organic framework, [Cu3(BTC)2] (BTC=benzene-1,3,5-tricarboxylate) was synthesized and used as a precursor for the synthesis of copper nanoparticles (NPs) and characterized by several techniques, including XRD, SEM, TEM, EDX and BET measurements. The as-synthesized copper nanoparticles were immobilized onto activated charcoal (AC) by means of ultrasonication at room temperature without any pretreatment. The Cu NPs/AC was employed as a heterogeneous catalyst for the cross-coupling of diphenyl diselenide and boronic acids to form diphenyl selenides through Se-Se bond activation under ligand-, base-, and additive-free conditions. The copper NPs/AC, which combines the architecture of MOFs and the high surface area of charcoal, could be an efficient heterogeneous catalytic system that is compatible with a variety of substituents on diphenyl selenides. Its promising catalytic activity relative to that of other homogeneous systems and low catalyst loading for the synthesis of unsymmetrical diaryl selenides is an important application in the area of nanocatalysis. The Cu NPs/AC catalyst, which exhibits excellent catalytic activity and remarkable tolerance to a wide variety of substituents, led to Se sp3-, sp2-, and sp-carbon bond formation by using DMSO as a solvent and atmospheric air as oxidant. This approach can also be extended to the preparation of unsymmetrical organotelluride derivatives. Three-in-one catalyst: Copper nanoparticles on activated charcoal show excellent catalytic activity towards the synthesis of unsymmetrical chalcogenides, starting from boronic acids, in air under ligand-, base-, and additive-free conditions, and resulting in selenium sp3-, sp2-, and sp-carbon bond formation.
- Mohan, Balaji,Yoon, Chohye,Jang, Seongwan,Park, Kang Hyun
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p. 405 - 412
(2015/03/04)
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- A convenient and efficient copper-catalyzed synthesis of unsymmetrical and symmetrical diaryl chalcogenides from arylboronic acids in ethanol at room temperature
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A simple and convenient approach for the synthesis of unsymmetrical diaryl chalcogenides (Te, Se, and S) has been developed by copper-catalyzed cross-coupling reaction of organoboronic acid with diaryl dichalcogenide in ethanol using NaBH4 in air or oxygen. The present methodology is highly practical for the synthesis of unsymmetrical diaryl tellurides with various functionalities such as -NO2, -F, -Br, and -COOH that have been obtained in good to excellent yields. Methodology is also effective for the synthesis of unsymmetrical diaryl selenides and sulfides. Moreover, symmetrical diaryl selenides have also been obtained from arylboronic acids using elemental selenium powder under optimized reaction conditions. The use of NaBH 4 is the key for the development of milder reaction conditions, which enable the construction of unsymmetrical diaryl chalcogenides from boronic acid substrates in ethanol at room temperature.
- Kumar, Amit,Kumar, Sangit
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p. 1763 - 1772
(2014/03/21)
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- Cu(ii) anchored nitrogen-rich covalent imine network (CuII-CIN-1): An efficient and recyclable heterogeneous catalyst for the synthesis of organoselenides from aryl boronic acids in a green solvent
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A new heterogeneous copper catalyst has been synthesized by immobilizing Cu(ii) onto the surface of a nitrogen rich porous covalent imine network material CIN-1 and it was characterized by powder X-ray diffraction (XRD), transmission electron microscopy (TEM), EDAX, X-ray photoelectron spectroscopy (XPS), N2 adsorption-desorption, UV-vis spectroscopy, Fourier transform infrared spectroscopy (FT-IR), thermogravimetric (TGA), and EPR spectroscopic analyses. The material has been successfully used to catalyze the cross-coupling reaction between aryl boronic acids and diphenyldiselenide to synthesize unsymmetrical organoselenides. Due to its high surface area and highly accessible catalytic sites, it shows good to excellent catalytic activity for the C-Se bond forming reaction, which was evident from the high TOF of the catalyst in this reaction. The catalyst was recycled for six repetitive runs without any appreciable loss of catalytic activity suggesting its potential usefulness in C-Se bond forming reaction. This journal is
- Roy, Susmita,Chatterjee, Tanmay,Banerjee, Biplab,Salam, Noor,Bhaumik, Asim,Islam, Sk Manirul
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p. 46075 - 46083
(2015/02/19)
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- Copper-catalyzed C-Se coupling of diphenyl diselenide with arylboronic acids at room temperature
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An efficient synthetic protocol for the Cu-catalyzed cross-coupling of diphenyl diselenide and arylboronic acid at room temperature was described. This catalytic system could tolerate a variety of arylboronic acids with only 3 mol % amount of CuSO4 as the catalyst and inexpensive 1,10-phen. H 2O as the ligand. Moreover, this catalytic system used environment-friendly EtOH as the solvent and catalytic amount of Na 2CO3 (20 mol %) as the base in the air.
- Zheng, Bo,Gong, Ying,Xu, Hua-Jian
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p. 5342 - 5347
(2013/06/27)
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- Reaction under ball-milling: Solvent-, ligand-, and metal-free synthesis of unsymmetrical diaryl chalcogenides
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A convenient, efficient, and general procedure for the synthesis of diaryl chalcogenides including sulfides, selenides and tellurides has been developed by the reaction of diazonium tetrafluoroborates and diaryl dichalcogenides on the surface of alumina u
- Mukherjee, Nirmalya,Chatterjee, Tanmay,Ranu, Brindaban C.
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p. 11110 - 11114
(2013/11/19)
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- Solvent-controlled halo-selective selenylation of aryl halides catalyzed by Cu(II) supported on Al2O3. A general protocol for the synthesis of unsymmetrical organo mono- and bis-selenides
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Alumina-supported Cu(II) efficiently catalyzes selenylation of aryl iodides and aryl bromides by diaryl, dialkyl, and diheteroaryl diselenides in water and PEG-600, respectively, leading to a general route toward synthesis of unsymmetrical diaryl, aryl-alkyl, aryl-heteroaryl, and diheteroaryl selenides. A sequential reaction of bromoiodobenzene with one diaryl/diheteroaryl/dialkyl diselenide in water and another diaryl/diheteroaryl/dialkyl diselenide in PEG-600 in the second step produces unsymmetrical diaryl, diheteroaryl, or aryl-alkyl bis-selanyl benzene. A library of functionalized organo mono- and bis-selenides, including a potent biologically active molecule and a couple of analogues of bioactive selenides, were obtained in high yields by this protocol. The reactions are chemoselective and high yielding. The Cu-Al2O 3 catalyst is recycled for seven runs without any appreciable loss of activity.
- Chatterjee, Tanmay,Ranu, Brindaban C.
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p. 7145 - 7153
(2013/08/23)
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- Microwave-assisted reaction of aryl diazonium fluoroborate and diaryl dichalcogenides in dimethyl carbonate: A general procedure for the synthesis of unsymmetrical diaryl chalcogenides
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A convenient, general and efficient procedure for the synthesis of unsymmetrical diaryl chalcogenides has been developed by the reaction of aryl diazonium fluoroborates and diaryl dichalcogenides in the presence of zinc dust in dimethyl carbonate under microwave irradiation. The reactions of a wide range of substituted aryl diazonium fluoroborates and diaryl dichalcogenides have been addressed. The zinc dust is required for the cleavage of diaryl dichalcogenides. The products are obtained in high purity after fast column chromatography of the crude residue after evaporation of dimethyl carbonate. The Royal Society of Chemistry 2012.
- Kundu, Debasish,Ahammed, Sabir,Ranu, Brindaban C.
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experimental part
p. 2024 - 2030
(2012/07/17)
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- CuS/Fe: A novel and highly efficient catalyst system for coupling reaction of aryl halides with diaryl diselenides
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The CuS catalyzed coupling reactions of aryl halides and diaryl diselenides were accelerated by the addition of Fe powder in only 3-12 h with good to excellent yields. SEM-EDX indicated that the in situ iron oxides as support against catalyst agglomeration accelerated the reaction. This catalyst system was also demonstrated recyclable without significant loss of catalytic activity.
- Li, Yaming,Wang, Huifeng,Li, Xiaoying,Chen, Tao,Zhao, Defeng
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supporting information; experimental part
p. 8583 - 8586
(2010/11/17)
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- Convenient synthesis of unsymmetrical organochalcogenides using organoboronic acids with dichalcogenides via cleavage of the S-S, Se-Se, or Te-Te bond by a copper catalyst
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(Chemical Equation Presented) This article describes the methodology for a copper-catalyzed preparation of numerous monochalcogenides from dichalcogenides with organoboronic acids. Unsymmetrical diorgano-monosulfides, selenides, and tellurides can be synthesized by the coupling of dichalcogenides with aryl- or alkylboronic acids using a copper catalyst in air. The present reaction can take advantage of both organochalcogenide groups on dichalcogenide.
- Taniguchi, Nobukazu
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p. 1241 - 1245
(2007/10/03)
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- Zinc-mediated synthesis of diaryl selenides from diaryl diselenides and diaryliodonium salts in aqueous media
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An efficient synthetic method has been developed for the preparation of symmetrical and unsymmetrical diaryl selenides through a one-pot reaction of diaryl diselenides and diaryliodonium salts in the presence of Zn/AlCl 3 system in aqueous media.
- Movassagh, Barahman,Fazeli, Azadeh
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p. 194 - 196
(2007/10/03)
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- Microwave-assisted copper-catalyzed preparation of diaryl chalcogenides
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Diaryl chalcogenide synthesis employing diaryl dichalcogenides and aryl halides as starting materials in the presence of excess magnesium and a catalytic amount of CuI/bipyridyl is significantly improved by microwave heating. Reaction times can be reduced from 2 to 3 days to 6-8 h. Both aryl bromides and aryl chlorides can be used as substrates in the substitution reaction. The procedure is useful not only for diaryl sulfide and diaryl selenide synthesis but also for the preparation of unsymmetrical diaryl tellurides. Starting from suitable aryl halides, the novel microwave-assisted procedure was used for the facile preparation of novel chalcogen analogues (PhS-, PhSe-, and PhTe-) of various antioxidants (ethoxyquin and 3-pyridinol). Attempts to use dialkyl dichalcogenides for the coupling of alkylchalcogeno moieties to aryl halides were only successful in the case of long-chain (such as n-octyl) disulfides and diselenides.
- Kumar, Sangit,Engman, Lars
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p. 5400 - 5403
(2007/10/03)
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- Copper-catalyzed synthesis of diaryl selenide from aryl iodide and diphenyl diselenide using magnesium metal
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Various unsymmetrical diaryl selenides can be synthesized from aryl iodides and diphenyl diselenide by an addition of magnesium metal in the presence of a copper catalyst. This method can exploit efficiently two phenylselenide-molecules generated from diphenyl diselenide under neutral conditions.
- Taniguchi, Nobukazu,Onami, Tetsuo
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p. 829 - 832
(2007/10/03)
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- Tributyltin aryl selenides as efficient arylselenating agents. Synthesis of diaryl and aryl organyl selenides
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Tributyltin aryl selenides are highly efficient arylselenating agents in reactions with aryl iodides and aryl triflates under catalysis with Pd and Ni complexes respectively. They also may be used as efficient source of active arylselenolate anion in the
- Beletskaya,Sigeev,Peregudov,Petrovskii
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p. 1463 - 1475
(2007/10/03)
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- New approaches to the synthesis of unsymmetrical diaryl selenides
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Unsymmetrical diaryl selenides PhSeAr were obtained by the palladium catalysed reactions of aryl (heteroaryl) iodide or triflate with Bu3SnSePh in high yields. The same compounds can be obtained by the non-catalytic reactions of Bu3SnSePh with ArN2BF4 or (ArN2)2ZnCl4.
- Beletskaya, Irina P.,Sigeev, Alexander S.,Peregudov, Alexander S.,Petrovskii, Pavel V.
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