- Synthesis of Unsymmetrical Diaryl Selenides: Copper-Catalyzed Se-Arylation of Diaryl Diselenides with Triarylbismuthanes
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Copper-catalyzed C(aryl)-Se bond formation by the reaction of diaryl diselenides with triarylbismuthanes in the presence of copper(I) acetate (10 mol%) and 1,10-phenanthroline (10 mol%) under aerobic conditions led to the formation of unsymmetric diaryl s
- Matsumura, Mio,Shibata, Kohki,Ozeki, Sota,Yamada, Mizuki,Murata, Yuki,Kakusawa, Naoki,Yasuike, Shuji
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- A new synthesis of highly active Rh-Co alloy nanoparticles supported on N-doped porous carbon for catalytic C-Se cross-coupling and p -nitrophenol hydrogenation reactions
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Bimetallic Rh-Co nanoparticles supported on nitrogen-doped porous carbon (Rh-Co/NPC) were synthesized from metal precursors and urea through a simple thermal decomposition/reduction under a nitrogen flow. The Rh-Co/NPC nanocatalyst which contains highly dispersed alloy nanoparticles (~6 nm) showed high catalytic performance as well as good recyclability for the C-Se coupling reaction of diphenyl diselenide and aryl boronic acid and p-nitrophenol reduction.
- Annas, Dicky,Lee, Hack-Keun,Hira, Shamim Ahmed,Park, Ji Chan,Park, Kang Hyun
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p. 7959 - 7966
(2021/05/21)
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- Metal-Free Synthesis of Unsymmetrical Aryl Selenides and Tellurides via Visible Light-Driven Activation of Arylazo Sulfones
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A protocol for the visible light driven preparation of unsymmetrical (hetero)aryl selenides and tellurides is described herein. The method exploits the peculiar photoreactivity of arylazo sulfones that act as thermally stable, precursors of aryl radicals under both photocatalyst- and additive-free conditions. The method developed shows an impressive versatility (more than fifty compounds isolated).
- Fagnoni, Maurizio,Li, Ankun,Li, Yuxuan,Liu, Junjie,Lu, Kui,Protti, Stefano,Shan, Xiwen,Tian, Miaomiao,Zhao, Xia
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supporting information
p. 7358 - 7367
(2020/12/01)
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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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- 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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- 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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- 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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- Magnetically separable and reusable copper ferrite nanoparticles for cross-coupling of aryl halides with diphenyl diselenide
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A simple and efficient procedure for the synthesis of diaryl selenides has been developed by a copper ferrite nanoparticle catalyzed reaction of aryl iodides/aryl bromides with diphenyl diselenide in the presence of base and solvent at 120 °C. Using this protocol, a variety of diselenides were obtained in good to excellent yields. The copper ferrite nanoparticles were magnetically separated, recycled, and reused up to three cycles. Copyright
- Swapna, Kokkirala,Murthy, Sabbavarapu Narayana,Nageswar, Yadavalli Venkata Durga
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experimental part
p. 1940 - 1946
(2011/04/27)
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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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- 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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- Solution-phase synthesis of diaryl selenides using polymer-supported borohydride.
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[reaction: see text] A new series of selenium-containing diaryl retinoids have been prepared by a new direct nickel(II)-catalyzed coupling of a diselenide with an iodoaryl in the presence of polymer-supported borohydride.
- Millois,Diaz
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p. 1705 - 1708
(2007/10/03)
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- Structural Study of Aryl Selenides in Solution Based on 77Se NMR Chemical Shifts: Application of the GIAO Magnetic Shielding Tensor of the 77Se Nucleus
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The 77Se NMR chemical shifts (δobsd(Se)) of p-YC6H4SeMe (1: Y = H (a), OMe (b), Me (c), Cl (d), Br (e), COOR (f), and NO2 (g)) and p-YC6H4SePh (2) were determined or redetermined
- Nakanishi, Waro,Hayashi, Satoko
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p. 6074 - 6081
(2007/10/03)
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