- Palladium Complex Immobilized on Magnetic Nanoparticles Modified with 2-Aminopyridine Ligand: A Novel and Efficient Recoverable Nanocatalyst for C–S and C–Se Coupling Reactions
-
A novel, versatile and efficient magnetically recoverable palladium nanocatalyst [Fe3O4@SiO2/2-aminopyridine-Pd(II)] was fabricated via the immobilization of palladium(II) complex on the surface of magnetic nanoparticles modified with 2-aminopyridine ligand. The structure of the as-fabricated Fe3O4@SiO2/2-aminopyridine-Pd(II) nanocomposite was characterized by a series of spectroscopic techniques including FT-IR, SEM, TEM, EDX, TGA, XRD, VSM and ICP-OES techniques. The Fe3O4@SiO2/2-aminopyridine-Pd(II) nanocomposite was utilized under mild and eco-friendly conditions in C–S and C–Se coupling reactions to afford a vast variety of diaryl sulfides and diaryl selenides with good to excellent yields. This heterogeneous palladium catalyst can be magnetically separated and reused for at least 7 consecutive trials without any reduction in activity. Graphical Abstract: [Figure not available: see fulltext.]
- Lu, Lu,Luo, Jia,Wang, Weiqi,Xu, Xiaoqing,Zhang, Jingzheng
-
-
- Trichloroisocyanuric Acid-Promoted Synthesis of Arylselenides and Aryltellurides from Diorganyl Dichalcogenides and Arylboronic Acids at Ambient Temperature
-
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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- Method for preparing asymmetric organic selenium ether compounds through metal-free chemical oxidation method (by machine translation)
-
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)
- -
-
Paragraph 0059-0063
(2020/12/09)
-
- Selenacalix[4]dithienothiophene: Synthesis, Structure, and Complexation of a Cyclic Tetramer of Selenide-Bridging Dithienothiophene
-
An efficient cyclization toward a cyclic tetramer of dithienothiophene (DTT) linked by divalent selenium atoms has been developed via palladium-catalyzed coupling reaction of (nBu3Sn)2Se. X-ray analysis revealed its highly symmetrical structure had an alternate arrangement of DTT units. There are several Se???π interactions forming a supramolecular network leading to large void channel space. The cyclic tetramer possesses moderate electron-donating ability. Furthermore, the cyclic tetramer undergoes complexation with C60 in a 1:2 ratio in the solid state to give a highly symmetrical three-dimensional array of C60.
- Hasegawa, Masashi,Takahashi, Kazuhiro,Inoue, Ryota,Haga, Shiori,Mazaki, Yasuhiro
-
supporting information
p. 1647 - 1650
(2018/09/21)
-
- New routes for the synthesis of unsymmetrical diarylselenides: Effect of heat, light and ultrasound
-
Herein, we report the photochemical coupling of diphenyldiselenides with substituted phenylhydrazine hydrochloride without catalyst. The protocol was developed not only in presence of sunlight and UV light but also under thermal condition for comparison study. Moreover, ultrasound assisted new catalytic protocol was developed using Ni(II)/L-proline system in DMSO with the advantage of shorter reaction time compared to earlier reports. We have also developed a new C-Se cross coupling reaction where phenylselenyl chloride and arylhydrazine hydrochlorides were effectively coupled using developed catalytic system.
- Sahani, Amber J.,Burange, Anand S.,Thakur, Seema D.,Jayaram, Radha V.
-
-
- Efficient heterogeneous copper-catalysed C–Se coupling of aryl iodides with symmetrical diselenides towards unsymmetrical monoselenides
-
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
-
p. 584 - 588
(2018/11/27)
-
- Synthesis of Diaryl Selenides via Palladium-Catalyzed Debenzylative Cross-Coupling of Aryl Benzyl Selenides with Aryl Bromides
-
Herein, we report a novel method for synthesizing diaryl selenides from aryl benzyl selenides and aryl bromides via debenzylative cross-coupling with a Pd/NIXANTPHOS-catalyst. NIXANTPHOS outperformed other commonly used bi- and monodentate ligands examined in this novel transformation. This reaction system displays wide functional group tolerance and excellent substrate scope. The transformation broadens the scope of palladium-catalyzed debenzylative processes to use selenolate anions as a leaving group. Its potential for practical synthetic applications was demonstrated with the gram scale synthesis of 4-chlorophenyl phenyl selenide.
- Wang, Hao,Chen, Shuguang,Liu, Guoqing,Guan, Haixing,Zhong, Daoyin,Cai, Jun,Zheng, Zhipeng,Mao, Jianyou,Walsh, Patrick J.
-
supporting information
p. 4086 - 4091
(2018/11/21)
-
- Composition for preventing or treating cancer comprising novel selenobenzene compound
-
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
- -
-
Paragraph 0086; 0092-0098
(2018/06/20)
-
- C-Se cross-coupling of arylboronic acids and diphenyldiselenides over non precious transition metal (Fe, Cu and Ni) complexes
-
Various tetradentate and tridentate ligands such as salophane, bishydrazone, bisbenzimidazolyl pyridine and isonicotinohydrazide have been prepared. Transition metal complexes of these ligands with Cu, Ni and Fe have been further synthesized and characterized by UV–vis, IR, NMR and CHN analysis. Catalytic activity of the metal complexes was tested for the cross coupling of diarylchalcogenide with arylboronic acid in DMSO as solvent in presence of a base. These non-precious metal complexes catalysed cross coupling reactions smoothly in shorter reaction time compared to earlier reports with comparable yields.
- Sahani, Amber J.,Jayaram, Radha V.,Burange, Anand S.
-
-
- Alternative Metal-Free Synthesis of Diorganoyl Selenides and Tellurides Mediated by Oxone
-
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
-
supporting information
p. 1479 - 1484
(2018/05/03)
-
- Atom-Economical Synthesis of Unsymmetrical Diaryl Selenides from Arylhydrazines and Diaryl Diselenides
-
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
-
p. 4928 - 4934
(2017/09/13)
-
- Visible-Light Photoredox Borylation of Aryl Halides and Subsequent Aerobic Oxidative Hydroxylation
-
Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use readily available aryl halides and bis(pinacolato)diboron as the starting materials, fac-Ir(ppy)3 as the photocatalyst, and corresponding arylboronic esters and phenols were obtained in good yields. The methods show some advantages including simple equipment, mild conditions, easy operation, and wide substrate scope. Therefore, they should provide a valuable strategy for chemical transformations.
- Jiang, Min,Yang, Haijun,Fu, Hua
-
supporting information
p. 5248 - 5251
(2016/11/02)
-
- Synthesis of Unsymmetrical Diaryl Selenides: Copper-Catalyzed Se-Arylation of Diaryl Diselenides with Triarylbismuthanes
-
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
-
p. 730 - 736
(2016/03/01)
-
- METHOD OF PREPARING CORE-SHELL COPPER NANOPARTICLES IMMOBILIZED ON ACTIVATED CARBON AND METHOD OF PREPARING CHALCOGENIDE COMPOUND USING NANOPARTICLES AS CATALYST
-
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.
- -
-
Paragraph 0056; 0065
(2016/11/14)
-
- Silver-Catalyzed Synthesis of Diaryl Selenides by Reaction of Diaryl Diselenides with Aryl Boronic Acids
-
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
-
supporting information
p. 11472 - 11476
(2016/11/28)
-
- A Highly Efficient Copper-Catalyzed Synthesis of Unsymmetrical Diaryl- and Aryl Alkyl Chalcogenides from Aryl Iodides and Diorganyl Disulfides and Diselenides
-
An efficient and convenient protocol has been developed for the copper-catalyzed reaction of aryl iodides and diorganyl disulfides and diselenides. A variety of symmetrical and unsymmetrical diaryl- and aryl alkyl chalcogenides were synthesized with good functional group tolerance and chemoselectivity by using copper(I) iodide as a catalyst, 4′-(4-methoxyphenyl)-2,2′:6′,2′′-terpyridine as ligand, and KOH as base under an inert atmosphere.
- Movassagh, Barahman,Hosseinzadeh, Zhila
-
supporting information
p. 777 - 781
(2016/03/12)
-
- A highly efficient and reusable MCM-41-immobilized bipyridine copper(I) catalyst for the C-Se coupling of organoboronic acids with diaryl diselenides
-
A highly efficient MCM-41-immobilized bipyridine copper(i) complex [MCM-41-bpy-CuI] was prepared from 4,4'-bis[3-(triethoxysilyl)propylaminomethyl]-2,2'-bipyridine via immobilization on the mesoporous material MCM-41, followed by reaction with CuI. In the presence of 5 mol% MCM-41-bpy-CuI, the cross-coupling reaction of organoboronic acids with diaryl diselenides proceeded smoothly in DMSO/H2O (2/1) at 110°C under air to afford a variety of diorganyl selenides in good to excellent yields. This heterogeneous copper catalyst can be recovered and recycled by a simple filtration of the reaction solution and used for at least 10 consecutive trials without any decrease in activity.
- Zhao, Hong,Jiang, Yuanyuan,Chen, Qiurong,Cai, Mingzhong
-
p. 2106 - 2115
(2015/03/18)
-
- Copper nanoparticles catalyzed Se(Te)-Se(Te) bond activation: A straightforward route towards unsymmetrical organochalcogenides from boronic acids
-
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
-
p. 405 - 412
(2015/03/04)
-
- Simple and catalyst-free method for the synthesis of diaryl selenides by reactions of arylselenols and arenediazonium salts
-
We describe here a simple and catalyst-free method to synthesize diaryl selenides by reaction of arenediazonium tetrafluoroborate salts with arylselenols, generated in situ by using diaryl diselenides and hypophosphorous acid (H3PO2), using THF as solvent. This is a direct nucleophilic aromatic substitution (SNAr) reaction performed with diaryl diselenides and arenediazonium salts bearing electron-withdrawing and electron-donating groups affording the corresponding diaryl selenides in moderated to good yields.
- Balaguez, Renata A.,Ricordi, Vanessa Gentil,Freitas, Camilo S.,Perin, Gelson,Schumacher, Ricardo F.,Alves, Diego
-
supporting information
p. 1057 - 1061
(2014/02/14)
-
- Simple and catalyst-free method for the synthesis of diaryl selenides by reactions of arylselenols and arenediazonium salts
-
We describe here a simple and catalyst-free method to synthesize diaryl selenides by reaction of arenediazonium tetrafluoroborate salts with arylselenols, generated in situ by using diaryl diselenides and hypophosphorous acid (H3PO2), using THF as solvent. This is a direct nucleophilic aromatic substitution (SNAr) reaction performed with diaryl diselenides and arenediazonium salts bearing electron-withdrawing and electron-donating groups affording the corresponding diaryl selenides in moderated to good yields.
- Balaguez, Renata A.,Ricordi, Vanessa Gentil,Freitas, Camilo S.,Perin, Gelson,Schumacher, Ricardo F.,Alves, Diego
-
supporting information
p. 1057 - 1061
(2015/02/19)
-
- A convenient and efficient copper-catalyzed synthesis of unsymmetrical and symmetrical diaryl chalcogenides from arylboronic acids in ethanol at room temperature
-
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
-
p. 1763 - 1772
(2014/03/21)
-
- An efficient one-pot approach to selenides: CuI-catalyzed reactions of magnesium selenolate with aryl or alkyl halides
-
An efficient one-pot route to symmetrical selenides in GC with yields from 13 to 94% has been developed by CuI catalyzing reactions of magnesium organoselenolates with aryl or alkyl halides under mild conditions. It is suggested that selenium could leave from PhSeMgBr to form other RSeMgBr with RMgBr based on experimental results. Although the leaving selenium causes low yield of unsymmetrical selenides and complex products, it offers a slowly releasing selenium source in preparation of nano metal selenides, and a potential leaving group in nucleophilic substitution. The role of excess magnesium is proposed.
- Gao, Fei,Tang, Yu,Lin, Hemei,Yang, Jun,Zhang, Yuanming
-
p. 787 - 793
(2013/07/26)
-
- Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides
-
A novel method of photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides has been developed. Although the arylation reactions with triarylbismuthines are usually catalyzed by transition-metal complexes, the present arylation of diaryl diselenides with triarylbismuthines proceeds upon photoirradiation in the absence of transition-metal catalysts. A variety of unsymmetrical diaryl selenides can be conveniently prepared by using this arylation method.
- Kobiki, Yohsuke,Kawaguchi, Shin-Ichi,Ohe, Takashi,Ogawa, Akiya
-
p. 1141 - 1147
(2013/07/26)
-
- Copper-catalyzed C-Se coupling of diphenyl diselenide with arylboronic acids at room temperature
-
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
-
p. 5342 - 5347
(2013/06/27)
-
- Magnetically separable CuFe2O4 nanoparticle catalyzed CSe cross coupling in reusable PEG medium
-
A simple and efficient procedure for the synthesis of unsymmetrical diaryl selenides has been developed by magnetically separable CuFe2O 4 nanoparticle catalyzed reactions of organoboranes with PhSeBr in recyclable PEG-400 medium at 80 °C and Cs2CO3 as base. Using this protocol, a variety of unsymmetrical selenides were obtained in good to excellent yields. The copper ferrite nanoparticles were magnetically separated, recycled, and reused up to four cycles.
- Harsha Vardhan Reddy,Satish,Ramesh,Karnakar,Nageswar
-
experimental part
p. 585 - 587
(2012/07/30)
-
- Glycerol as a recyclable solvent for copper-catalyzed cross-coupling reactions of diaryl diselenides with aryl boronic acids
-
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
-
supporting information; experimental part
p. 1030 - 1034
(2012/06/04)
-
- Synthesis of diaryl selenides using electrophilic selenium species and nucleophilic boron reagents in ionic liquids
-
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
-
supporting information; experimental part
p. 2931 - 2938
(2011/11/29)
-
- Magnetically separable and reusable copper ferrite nanoparticles for cross-coupling of aryl halides with diphenyl diselenide
-
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
-
experimental part
p. 1940 - 1946
(2011/04/27)
-
- Palladium-catalyzed cross-coupling of PhSeSnBu3 with aryl and alkyl halides in ionic liquids: A practical synthetic method of diorganyl selenides
-
Palladium-catalyzed cross-coupling reactions of phenyl tributylstannyl selenide with aryl and alkyl halides can proceed smoothly in room temperature ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF 6]), to give the corresponding diorganyl selenides in good to high yields. The coupling reaction run in [bmim][PF6] has the advantages of rate acceleration and increase of yield in contrast to the reaction run in toluene. Our system not only avoids the use of easily volatile toluene as a solvent but also solves the basic problem of palladium catalyst reuse.
- Zhao, Hong,Hao, Wenyan,Xi, Zhiwen,Cai, Mingzhong
-
experimental part
p. 2661 - 2665
(2012/01/04)
-
- An efficient copper(I) iodide catalyzed synthesis of diaryl selenides through Cse bond formation using solvent acetonitrile as ligand
-
A wide range of diaryl selenides can be synthesized through CSe bond formation using readily available copper(I) iodide as catalyst under mild reaction conditions (82C) from aryl iodides and diphenyl diselenide. In this coupling reaction, solvent acetonitrile acts as ligand for copper(I) iodide and no external ligand is required. Less reactive aryl bromides also provide the di-aryl selenides in good isolated yields. Georg Thieme Verlag Stuttgart ? New York.
- Dandapat, Arpan,Korupalli, Chiranjeevi,Prasad,Singh, Rahul,Sekar, Govindasamy
-
experimental part
p. 2297 - 2302
(2011/09/16)
-
- Al2O3-Supported Cu-catalyzed electrophilic substitution by PhSeBr in organoboranes, organosilanes, and organostannanes. A protocol for the synthesis of unsymmetrical diaryl and alkyl aryl selenides
-
(Figure Presented) Alumina-supported copper sulfate efficiently catalyzes electrophilic substitution in organoborane, organosilanes, and organostannanes by phenylselenium bromide providing a novel and efficient route to the synthesis of unsymmetrical diaryl and alkyl aryl selenides. A series of aryl, alkyl, and heteroaryl phenyl selenides were obtained in high yields. The catalyst is inexpensive, eco- and user-friendly, and recyclable. The mechanism involving Cu-assisted nucleophilic displacement of Br in PhSeBr by mild nucleophiles is described.
- Bhadra, Sukalyan,Saha, Amit,Ranu, Brindaban C.
-
experimental part
p. 4864 - 4867
(2010/10/18)
-
- CuS/Fe: A novel and highly efficient catalyst system for coupling reaction of aryl halides with diaryl diselenides
-
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
-
supporting information; experimental part
p. 8583 - 8586
(2010/11/17)
-
- Copper oxide nanoparticle-catalyzed coupling of diaryl diselenide with aryl halides under ligand-free conditions
-
A new, efficient and ligand-free cross-coupling reaction of aryl halides and diaryl diselenides using a catalytic amount of nanocrystalline CuO as a recyclable catalyst with KOH as the base in DMSO at 110 °C is reported. This protocol has been utilized for the synthesis of a variety of aryl selenides in excellent yields from the readily available aryl halides and diaryl diselenides.
- Reddy, Vutukuri Prakash,Kumar, Akkilagunta Vijay,Swapna, Kokkirala,Rao, Kakulapati Rama
-
supporting information; experimental part
p. 951 - 953
(2009/07/11)
-
- Eco-friendly cross-coupling of diaryl diselenides with aryl and alkyl bromides catalyzed by CuO nanopowder in ionic liquid
-
An eco-friendly cross-coupling reaction of aryl and alkyl bromides with diselenides using a catalytic amount of CuO nanopowder as a catalyst and an ionic liquid as a recyclable solvent is reported. The system shows high efficiency to catalyze this transformation, and in a green fashion due to the recyclable approach and the non-residual design protocol. This procedure has been utilized for the synthesis of a variety of diaryl selenides in good to excellent yields from the readily available aryl and alkyl bromides and diselenides. The Royal Society of Chemistry 2009.
- Singh, Devender,Alberto, Eduardo E.,Rodrigues, Oscar Endrigo Dorneles,Braga, Antonio Luiz
-
experimental part
p. 1521 - 1524
(2010/06/13)
-
- CuO nanoparticles: an efficient and recyclable catalyst for cross-coupling reactions of organic diselenides with aryl boronic acids
-
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.
-
scheme or table
p. 6635 - 6638
(2010/03/01)
-
- Lanthanum(III) oxide as a recyclable catalyst for the synthesis of diaryl sulfides and diaryl selenides
-
La2O3 as a new and efficient recyclable catalyst in coupling various aryl halides with aromatic/alkyl thiols and diphenyl diselenide in combination with KOH as a base and DMEDA as a ligand in DMSO at 110 °C is reported.
- Murthy, Sabbavarapu Narayana,Madhav, Bandaru,Reddy, Vutukuri Prakash,Nageswar, Yadavalli Venkata Durga
-
supporting information; experimental part
p. 5902 - 5905
(2010/03/02)
-
- 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
-
(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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- Palladium-catalyzed coupling reaction of diaryl dichalcogenide with aryl bromide leading to the synthesis of unsymmetrical aryl chalcogenide
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An efficient cross-coupling reaction of diphenyl disulfide or diselenide with substituted aryl bromides using PdCl2(dppf) and zinc has been developed. This method gave functionalized unsymmetrical aryl sulfides and selenides in good to excellent yields under neutral conditions. Georg Thieme Verlag Stuttgart.
- Fukuzawa, Shin-Ichi,Tanihara, Daisuke,Kikuchi, Satoshi
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p. 2145 - 2147
(2008/02/05)
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- CsOH·H2O promoted areneselenenylation of aryl bromides and iodides
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We report a transition metal-free synthetic protocol for the cross-coupling reaction of aryl bromides and aryl iodides and diphenyl diselenide (Ph 2Se2) using CsOH·H2O as a base in DMSO at 110°C. Using this protocol, we show that a variety of diaryl selenides can be synthesized in moderate to good yields.
- Varala, Ravi,Ramu, Enugala,Adapa, Srinivas R.
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p. 140 - 141
(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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- Methods for formation of aryl-sulfur and aryl-selenium compounds using copper(I) catalysts
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A mild, palladium-free synthetic protocol for the cross-coupling reaction of vinyl or aryl iodides and thiols or selenols using, in certain embodiments, 10 mol % CuI and 10 mol % neocuproine, with NaOt-Bu as the base, in toluene at 110 ° C. A variety of vinyl/aryl sulfides and vinyl/aryl selenides can be synthesized in excellent yields from readily available iodides and thiols or selenols.
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Page/Page column 13-14; 35-36
(2008/06/13)
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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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- A simple copper salt-catalyzed synthesis of unsymmetrical diaryl selenides and tellurides from arylboronic acids with diphenyl diselenide and ditelluride
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In the presence of a catalytic amount of simple copper salt, the reaction of arylboronic acids with diphenyl diselenide and ditelluride was accomplished without any additive to afford the corresponding unsymmetrical diarylselenides and tellurides in good yields. Georg Thieme Verlag Stuttgart.
- Wang, Lei,Wang, Min,Huang, Fuping
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p. 2007 - 2010
(2007/10/03)
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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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p. 915 - 920
(2007/10/03)
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- A general method for the formation of diaryl selenides using copper(I) catalysts
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We report a mild, palladium-free synthetic protocol for the cross coupling reaction of aryl iodides and phenyl selenol using 10 mol% CuI/neocuproine, NaOt-Bu or K2CO3 as base, in toluene, at 110°C. Using this protocol, we show that a variety of diaryl selenides can be synthesized in good yields from commercially available aryl iodides.
- Gujadhur, Rattan K.,Venkataraman
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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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- The role of ate complexes in the lithium-sulfur, lithium-selenium and lithium-tellurium exchange reactions
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Hypervalent ate complexes are presumptive intermediates in the metal-halogen, metal-tellurium, and related exchange reactions. The effect of o,o′-biphenyldiyl vs. diphenyl substitution on formation of tellurium ate complexes was studied by a kinetic technique and by NMR spectroscopy. Only a modest increase in the association constant (Kate) was measured. When Li/M exchanges of o,o′-biphenyldiyl sulfides and selenides were made intramolecular by means of a m-terphenyl framework (12-S, 12-Se, 21), enormous increases (> 109) in the rate of Li/S and Li/Se exchange were observed compared to acyclic models. Apparently, these systems are ideally preorganized to favor the T-shaped geometry of the hypervalent intermediates. For the selenium systems, ate complex intermediates (20-Se, 26) were detected spectroscopically in THF- or THF/HMPA-containing solutions. A DNMR study showed that Li/Se exchange was substantially faster than exchange of the lithium reagents with the ate complex. Therefore, these ate complexes are not on the actual Li/Se exchange pathway.
- Reich, Hans J.,Gudmundsson, Birgir Oe.,Green, D. Patrick,Bevan, Martin J.,Reich, Ieva L.
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p. 3748 - 3772
(2007/10/03)
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- Insertion of selenium into zinc carbon bonds and its application in the synthesis of unsymmetrical diarylselenides
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Selenium inserts into the zinc carbon bond of aryl zinc halides to form the corresponding zinc selenoates; these react in THF-HMPA with diaryliodonium salts to afford unsymmetrical diaryl selenides in good yields.
- Xu, Xin-Hua,Liu, Wen-Qi
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p. 444 - 445
(2007/10/03)
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- New synthetic method of diorganyl selenides: Palladium-catalyzed reaction of PhSeSnBu3 with aryl and alkyl halides
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(formula presented) Palladium complexes such as Pd(PPh3)4 catalyzed the reaction of phenyl tributylstannyl selenide (PhSeSnBu3) with aryl and alkyl halides, giving the corresponding diaryl and alkylaryl selenides in moderate to good yields.
- Nishiyama, Yutaka,Tokunaga, Keiji,Sonoda, Noboru
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p. 1725 - 1727
(2008/02/11)
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