- 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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- Palladium Nanoparticles Supported on Nitrogen-rich Containing Melamine-based Microporous Covalent Triazine Polymers as Efficient Heterogeneous Catalyst for C?Se Coupling Reactions
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In the present work, microporous nitrogen containing covalent triazine polymers (CTPs) TATAM was synthesized from condensation of 4,4′4′′-(1,3,5-triazine-2,4,6-triyl) tribenzaldehyde (TATA) and melamine under solvothermal conditions to obtain nitrogen- rich triazine containing polymeric supported materials (TATAM). Further, palladium nanoparticles (Pd NPs) were supported on TATAM polymeric networks (Pd@TATAM). The synthesized Pd@TATAM CTPs material was thoroughly characterized by FT-IR, UV-DRS, solid state 13C-CPMAS, XPS, powder X-ray diffraction, TGA, SEM, TEM. In addition, the characterized Pd@TATAM CTPs were applied to check the catalytic application. The Pd@TATAM was shown to be an efficient and reusable heterogeneous solid catalyst for the formation of C?Se bond through coupling of aryl halide and elemental selenium, dimethyl sulfoxide as a solvent at 100 °C for about 6 h. Besides the absence of metal leaching for catalytic system, it is also observed that the catalyst can be reused for three consecutive cycles with a minimal decrease in its activity.
- Sadhasivam, Velu,Balasaravanan, Rajendiran,Chithiraikumar, Chinnadurai,Siva, Ayyanar
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- Deoxygenation and other photochemical reactions of aromatic selenoxides
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Atomic oxygen O(3P) is a potent oxidant that has been well-studied in the gas phase. However, exploration of its reactivity in the condensed organic phase has been hampered by the lack of an appropriate source. Dibenzothiophene-S-oxide (DBTO) and related derivatives have been promoted as photochemical D(3P) sources but suffer from low quantum yields. Photolysis of dibenzoselenophene-Se-oxide (DBSeO) results in the formation of dibenzoselenophene and oxidized solvent in significantly higher quantum yields, ca. 0.1. The oxidation product ratios from toluene obtained from the photolysis of dibenzothiophene-S-oxide and the corresponding selenoxide are the same, strongly suggesting a common oxidizing intermediate, which is taken to be O(3P). An additional product, proposed to be the corresponding selenenic ester, is also observed under deoxygenated conditions. The photochemistry of diphenyl selenoxide includes a minor portion of oxidant-forming deoxygenation, in contrast to previous conclusions.
- McCulla, Ryan D.,Jenks, William S.
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- Ullmann-type C-Se Cross-Coupling in the Hydantoin Family: Synthesis, Mechanistic Studies, and Tests of Biological Activity
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An attractive strategy for C-Se bond formation by Ullmann-type copper(I)-promoted cross-coupling is developed. A wide range of aryliodides reacts with various disubstituted 2-selenohydantoins under mild conditions and provides Se-arylated imidazolines in moderate to high yields. Computational mechanistic studies show the oxidative addition/intramolecular reductive elimination likely to be the lowest-energy pathway. Cytotoxic activity of all 43 reaction products has been tested in vitro against MCF7 and A549 cancer cell lines with VA13 and MCF10a control cells.
- Beloglazkina, Elena K.,Finko, Alexander V.,Laikov, Dimitri N.,Majouga, Alexander G.,Skvortsov, Dmitry A.,Tafeenko, Victor A.,Vyhivskyi, Oleksandr,Zhirkina, Irina V.,Zyk, Nikolay V.
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- Synthesis of 9-oxoselenoxanthenium and triarylselenonium hexafluorophosphates
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The selenoxides forming 9-oxoselenoxanthenium and triaryl selenonium hexafluorophosphates via interaction with heptyl phenyl ether and anisole in the MeSO3H-P2O5 mixture followed by treatment with KPF6 have been obtained via selenoxantene-9-one and diphenyl selenide derivatives oxidation with m-chloroperoxybenzoic acid or hydrogen peroxide.
- Loskutov,Balina,Russkikh,Shelkovnikov
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- Simple and efficient copper-catalyzed synthesis of symmetrical diaryl selenides from triarylbismuthanes and selenium under aerobic conditions
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Symmetrical diaryl selenides were synthesized in moderate-to-excellent yields by Cu-catalyzed C(aryl)–Se bond formation followed by the reaction of triarylbismuthanes with elemental Se in the presence of Cu(OAc)2 and 1,10-phenanthroline (10 mol%) under aerobic conditions. This reaction proceeded efficiently: All the aryl groups on Bi were transferred to the coupling products.
- Matsumura, Mio,Kumagai, Hanae,Murata, Yuki,Kakusawa, Naoki,Yasuike, Shuji
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- Synthesis of diaryl selenides using the in situ reagent SeCl2
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Reactions of in situ prepared SeCl2 with Grignard reagents (prepared from bromobenzene, o-tolyl bromide, 2,6-dimethyl-4-tert-butyl-1- bromobenzene, and 1-bromo-2-methylnaphthalene) and dilithiated benzamides (prepared from N-phenyl, N-cyclohexyl, and N-isopropyl benzamide) are described.
- Zade, Sanjio S.,Panda, Snigdha,Singh, Harkesh B.,Wolmersh?user, Gotthelf
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- A novel stereoselective preparation of various vinyl sulfide derivatives using β-alkylthioalkenylselenonium salts
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The treatment of alkynylselenonium salt and various thiophenol derivatives with a catalytic amount of triethylamine gave β-arylthioalkenylselenonium salts in good yields. The alkenylselenonium salts thus prepared reacted with nucleophiles such as acetylides, thiolates, and alkoxides to produce (Z)-β-arylthio-α-functionalized ethenes in high yields. The vinylselenonium salts bearing a hydroxy group on a β-side chain caused intramolecular cyclization upon treatment with sodium hydride to produce medium-membered heterocyclic compounds containing sulfur and oxygen atoms. The reactions giving (Z)-β-arylthio-α-functionalized ethenes would proceed via the formation of selenurane intermediates followed by the ligand coupling reaction.
- Watanabe,Mori,Nagai,Iwamura,Iwama,Kataoka
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- Selenium dioxide promoted dinitrogen extrusion/direct selenation of arylhydrazines and anilines
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A novel, efficient, economical strategy for the coupling and direct selenation of arylhydrazines to selenides using SeO2 has been developed. Our method employs SeO2 as the selenium source with hydrazines as coupling reactants to generate selenides via dinitrogen extrusion. This reagent also helped to generate ArSe substitued aniline derivatives via C–H functionalization reaction in good yields. The application of this method in gram scale was also carried out.
- Yaqoob Bhat, Mohammad,Kumar, Atul,Naveed Ahmed, Qazi
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- Introduction of alkyl- or phenylseleno group by the ring opening of cyclic ethers using dialkyl- or alkylphenylselenium dibromide and sodium borohydride
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The reaction of dialkyl- or alkylphenylselenium dibromide with cyclic ethers in the presence of sodium borohydride gave ω-hydroxyalkyl alkyl or phenyl selenides as the ring opening products of the cyclic ethers.
- Takanohashi,Funakoshi,Akabori
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- SRN1 reaction of haloarenes with benzenethiolate, benzeneselenolate, and benzenetellurolate ions promoted by Sml2
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SRN1 reaction is of haloarenes with benzenethiolate, benzeneselenate, and benzenetellurolate ions can be carried out by use of samarium diiodide (SmI2) as a promoter in DMF-THF to afford the corresponding ArZPh compounds in moderate to good yields.
- Zhang, Yongmin
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- Eco-friendly cross-coupling of diaryl diselenides with aryl and alkyl bromides catalyzed by CuO nanopowder in ionic liquid
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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
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- Kinetic studies on the ligand coupling reactions of tetraphenyl sulfurane, selenurane, and tellurane. Thermal stability for hypervalent chalcogen compounds with four carbon-chalcogen bonds
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Ligand coupling kinetics of tetraphenyl sulfurane, selenurane, and tellurane have been studied by the variable temperature NMR experiments. The first examples of the activation parameters for the ligand coupling (self decomposition and C-C bond formation) have been obtained for the reactions at three pentacoordinated chalcogenium centers; S, Se, Te.
- Ogawa,Sato,Furukawa
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- Potassium selenocyanate as an efficient selenium source in C-Se cross-coupling catalyzed by copper iodide in water
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An efficient and conceptually new protocol for C-Se cross coupling of potassium selenocyanate with aryl halides via copper-catalyzed cascade reaction has been developed in water. Utilizing this protocol, a variety of aryl and heteroaryl halides were reacted with potassium selenocyanate to afford the corresponding diaryl selenides in moderate to good yields.
- Kumar, A. Vijay,Reddy, V. Prakash,Reddy, C. Suresh,Rao, K. Rama
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- NOVEL REDUCTION OF CHLORINE ADDUCTS OF ARYL AND ALKYL SELENIDES WITH DIMETHYL SULFOXIDE
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The adducts of chlorine with diaryl selenides such as selenanthrene, diphenyl selenide, and selenoxanthone have been found to be reduced to the corresponding selenides in dimethyl sulfoxide forming chloromethyl methyl sulfoxide and hydrogen chloride.Similarly, dimethyl selenide dichloride was reduced to dimethyl selenide in the presence of a base.
- Nakanishi, Waro,Sakaue, Akira,Ikeda, Yoshitsugu,Iwamura, Hiizu
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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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- Synthesis, characterization, structures and GPx mimicking activity of pyridyl and pyrimidyl based organoselenium compounds
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Pyridyl and pyrimidyl based organoselenium compounds have been synthesized and characterized by analytical and spectroscopic techniques. Molecular structures of 2,2′-dipyrimidyl diselenide (1b), 2,2′-dipyrimidyl selenide (2b) and 2-pyrimidyl seleno ethanoic acid (3d) have been determined by single crystal X-ray diffraction analyses. The 3d is associated in the solid state through hydrogen bonding between carboxylic acid proton and N2 of the pyrimidyl ring of an adjacent molecule. The in vitro GPx-like catalytic activity for these compounds was evaluated by 1H NMR and HPLC methods where H2O2 was reduced by dithiothreitol (DTTred) and glutathione (GSH) as a thiol cofactor, respectively, in the presence of catalytic amounts of organoselenium compounds. The electron density around selenium atom (-SeSe- or -Se-) which is reflected by 77Se{ 1H} NMR chemical shifts, has been found to be one of the crucial factors in influencing their overall GPx like activity.
- Hodage, Ananda S.,Parashiva Prabhu, C.,Phadnis, Prasad P.,Wadawale, Amey,Jain, Vimal K.,Priyadarsini, K. I.
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- A convenient method for the preparation of diaryl tellurides and diaryl selenides
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Sodium hydrogen telluride or selenide reacts rapidly with aryldiazonium fluoborates to give the corresponding symmetric diaryl tellurides or selenides.
- Chen,Qiu,Zhou
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- Ni nanoparticle-confined covalent organic polymer directed diaryl-selenides synthesis
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The present work describes the preparation of a new covalent organic polymer (COP) and its application as a hetero support for diaryl selenides synthesis. A nitrogen rich COP (CGP) has been synthesized via SNAr reaction of cyanuric chloride with guanidinium hydrochloride. The successful confinement of COP with Ni nanoparticles through post-synthetic transformations (Ni?CGP) provides excellent catalytic activity for the transformation of aryl halides into diaryl selenides using elemental selenium powder. The synthetic transformations are well confirmed using various modern analytical and spectroscopic techniques which reveal high chemical and thermal durability. The N-rich framework of CGP fortifies the confinement of Ni NPs. Ni?CGP provides an efficient approach for diaryl selenides synthesis using a very cheap selenating reagent under water benign solvent conditions (DMSO?:?H2O) at room temperature with high reusability. Significantly, our work not only contributes the opportunity for developing economical and effective non-noble metal decorated COPs as heterogeneous catalysts, but also delivers an efficient approach to produce industrially important C-Se coupling products.
- Awasthi, Satish Kumar,Dixit, A. K.,Raghothama, S.,Yadav, Deepika
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- Environmentally Friendly and Recyclable CuCl 2-Mediated C-S Bond Coupling Strategy Using DMEDA as Ligand, Base, and Solvent
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Simple reaction conditions and recyclable reagents are crucial for environmentally friendly industrial applications. An environment-friendly, recyclable and economic strategy was developed to synthesize diaryl chalcogenides by the CuCl2-catalyzed C S bondformation reaction via iodobenzenes and benzenethiols/1,2-diphenyldisulfanes using N,N'-dimethylethane-1,2-diamine (DMEDA) as ligand, base, and solvent. For these reactions, especially the reactions of diiodobenzenes and aminobenzenethiols/disulfanediyldianilines, a range of substrates are compatible and give the corresponding products in good to excellent yields. Both of the reagents in the catalytic system (CuCl2/DMEDA) are inexpensive, conveniently separable, and recyclable for more than five cycles.
- Shen, Guodong,Lu, Qichao,Wang, Zeyou,Sun, Weiwei,Zhang, Yalin,Huang, Xianqiang,Sun, Manman,Wang, Zhiming
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supporting information
p. 184 - 198
(2021/09/20)
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- Green Synthesis of Diaryl Selenides from Arylboronic Acids and Arylseleninic Acids
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A new method of deborylative selanylation using arylboronic acids and arylseleninic acids gave diaryl selenoethers and diarylselenoxide. The present approach requires only equimolar arylseleninic acid and led selectively to selenoethers or selenoxides depending on the solvent. The method is metal-free, base- or oxidant-free, efficient, and environmentally friendly.
- Redon, Sébastien,Remusat, Vincent,Vanelle, Patrice
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supporting information
p. 483 - 487
(2022/02/21)
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- Nickel-Catalyzed Intramolecular Decarbonylative Coupling of Aryl Selenol Esters
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This report describes a method for Ni-catalyzed intramolecular decarbonylative coupling, which enables the conversion of areneselenol esters to diaryl selenides. The inexpensive and readily available catalyst can be employed under mild reaction conditions for the construction of structurally diverse diaryl selenides, including heterocyclic and natural product derivatives. (Figure presented.).
- Bai, Jin-Hua,Qi, Xiu-Juan,Sun, Wei,Yu, Tian-Yang,Xu, Peng-Fei
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p. 2084 - 2088
(2021/03/01)
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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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- 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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- 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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- Late to the Party: Synthesis and Characterization of Tellurium and Selenium Half-Sandwich Complexes
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We report the synthesis and characterization of the first series of tellurium and selenium complexes featuring an ν5-cyclopentadienyl ligand. Reaction of Ph3TeX (X = Cl, S2CNEt2) with MCpR (M = Li, K; R = H, Me4, Me5) results in high yields of [Cp][TePh3] (1), [CpMe4][TePh3] (2), and [Cp*][TePh3] (3), respectively. Similarly, reaction of Ph3SeCl with LiCp and KCp? furnishes [Cp][SePh3] (4) and [Cp*][SePh3] (5). Each was characterized by X-ray crystallography, revealing similar ν5-coordination with little distortion from an idealized half-sandwich geometry, presumably from the remaining lone pair on tellurium and selenium. The Te-centroid distances are relatively long (1: 2.770(3), 2: 2.746(1), and 3: 2.733(1) ?), suggesting a mostly ionic interaction. Se-centroid distances (4: 2.748(3), 5: 2.707(2), 2.730(2) ?) were found to be surprisingly similar despite its smaller atomic radius. Compounds 2, 3, and 5 display rapid decomposition at room temperature, extruding a phenylated cyclopentadiene and the respective diphenylchalcogenide. The nature of bonding within these complexes was investigated through DFT methods and found to be primarily ionic in nature.
- Bart, Suzanne C.,Jones, Leighton O.,Kieser, Jerod M.,Schatz, George C.,Uible, Madeleine C.,Zeller, Matthias
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supporting information
p. 4104 - 4109
(2021/12/17)
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- Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis
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An application for dechalcogenization of aryl dichalcogenides via copper catalysis to synthesize aryl chalcogenides is disclosed. This approach is highlighted by the practical conditions, broad substrate scope, and good functional group tolerance with several sensitive groups such as aldehyde, ketone, ester, amide, cyanide, alkene, nitro, and methylsulfonyl. Furthermore, the robustness of this methodology is depicted by the late-stage modification of estrone and synthesis of vortioxetine. Remarkably, synthesis of more challenging organic materials with large ring tension under milder conditions and synthesis of some halogen contained diaryl sulfides which could not be synthesized using metal-catalyzed coupling reactions of aryl halogen are successfully accomplished with this protocol.
- Cao, Fei,Chen, Jinhong,Deng, Jiedan,Deng, Xuemei,Hou, Yongsheng,Shao, Xiangfeng,Shi, Tao,Wang, Yongqiang,Wang, Zhen,Wu, Lingxi,Yang, Jinru,Yang, Yuhang
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p. 2707 - 2712
(2020/03/11)
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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 0031-0058
(2020/12/09)
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- Novel and facile procedure for the synthesis of Ni(II) and Pd(II) PSCOP pincer complexes. Evaluation of their catalytic activity on C-S, C-Se and C-C cross coupling reactions
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A new and facile procedure for the synthesis of non-symmetric phosphinito-thiophosphinito PSCOP pincer complexes based on Ni(II) and Pd(II) was developed. The synthesis of the complexes was carried out in a single step, starting from 3,3-dihydroxydiphenyldisulfide. The Ni(II) complexes were tested as catalysts in C-S and C-Se coupling reactions, being the tBu derivative 3-Ni the one exhibiting the best performance in both transformations. In this case, the sterics of the substrates was studied, showing that higher steric hindrance leads to lower yields. Analogously, the Pd(II) complexes were used as catalyst in Suzuki-Miyaura couplings of para-substituted bromobenzenes and phenyl boronic acid, being the analogous tBu derivative complex 3-Pd the best catalysts for this process, exhibiting tolerance to a wide range of functional groups.
- Valderrama-García, Bianca X.,Rufino-Felipe, Ernesto,Valdés, Hugo,Hernandez-Ortega, Simón,Aguilar-Castillo, Bethsy Adriana,Morales-Morales, David
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- Nickel-catalyzed and Li-mediated regiospecific C-H arylation of benzothiophenes
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A nickel-based catalytic system for the regiospecific C2-H arylation of benzothiophene has been established. NiCl2(bpy) is used as a catalyst in combination with LiHMDS as a base in dioxane. The catalytic system is applicable to a variety of functionalized benzothiophenes, as well as other heteroarenes including thiophene, benzodithiophene, benzofuran and selenophene in combination with iodo aryl electrophiles. The role of LiHMDS as a uniquely potent base and a postulated mechanism are discussed. The applicability of this system is finally demonstrated for the synthesis of an intermediate of an active pharmaceutical ingredient.
- Canivet, Jér?me,Grousset, Léonie,Hisler, Ga?lle,Mohr, Yorck,Quadrelli, Elsje Alessandra,Roux, Yoann,Wisser, Florian M.
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p. 3155 - 3161
(2020/06/19)
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- Preparation method of selenium thioether compounds
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The invention discloses a preparation method of selenium thioether compounds. According to the method, S-S (Se-Se) bonds can be effectively oxidized and cracked under the action of catalytic amount oftrifluoromethanesulfonic acid and diethyl azodicarboxylate, positive sulfur ions or positive selenium ions are generated, and the positive ions receive attack of different nucleophilic reagents, so that various types of selenium thioether compounds can be acquired. Cyclized alkyl selenium thioether compounds can be efficiently acquired by the method when olefine acid and olefinic alcohol or enamine serve as substrates. Asymmetric aryl selenium thioether compounds can be synthesized by the method when arylboronic acid or aromatic rings serve as a substrate. The preparation method is simple andeasy to operate, rapid, convenient, mild in condition, good in region-selectivity and high in yield, metal participation is omitted, and various types of selenium thioether compounds can be efficiently synthesized.
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Paragraph 0040-0044
(2019/01/23)
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- A cost-effective shortcut to prepare organoselenium catalysts via decarboxylative coupling of phenylacetic acid with elemental selenium
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An interesting decarboxylative coupling reaction of phenylacetic acid with elemental selenium was discovered and employed for the preparation efficient organoselenium catalysts for Baeyer–Villiger reaction and oxidative deoximation reaction. Compared with the traditionally used Grignard reagent method, the decarboxylative coupling reaction with selenium powders provides a shortcut for the preparation of organoselenium catalysts free of carcinogenic organohalide starting materials, toxic and odorous selenol intermediates and magnesium salt solid wastes. This may be helpful for reducing the cost of selenium catalysts to facilitate the application of organoselenium-catalyzed green reactions in large-scale production.
- Cao, Hongen,Liu, Mingxuan,Qian, Rongrong,Zhang, Xu,Yu, Lei
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- Selenacalix[4]dithienothiophene: Synthesis, Structure, and Complexation of a Cyclic Tetramer of Selenide-Bridging Dithienothiophene
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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
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supporting information
p. 1647 - 1650
(2018/09/21)
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- New routes for the synthesis of unsymmetrical diarylselenides: Effect of heat, light and ultrasound
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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.
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- C-Se cross-coupling of arylboronic acids and diphenyldiselenides over non precious transition metal (Fe, Cu and Ni) complexes
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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.
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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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- 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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- Thorium Cubanes-Synthesis, Solid-State and Solution Structures, Thermolysis, and Chalcogen Exchange Reactions
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Thorium cubanes (py)8Th4(μ3-E′)4(μ2-EPh)4(ν-EPh)4 (E, E′ = S, Se) were prepared from ligand-based redox reactions of elemental E′ with Th(EPh)4. Products with all four
- Ringgold, Marissa,Rehe, David,Hrobárik, Peter,Kornienko, Anna Y.,Emge, Thomas J.,Brennan, John G.
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p. 7129 - 7141
(2018/06/22)
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- CATALYTIC C-X-BOND METATHESIS THROUGH ARYLATION
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The present invention refers to a process for a catalytic aryl transfer to rearrange the backbone of aromatic C-X bonds.
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Page/Page column 27; 28
(2018/09/28)
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- Synthesis of Diaryl Selenides via Palladium-Catalyzed Debenzylative Cross-Coupling of Aryl Benzyl Selenides with Aryl Bromides
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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.
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supporting information
p. 4086 - 4091
(2018/11/21)
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- Copper-Silver Dual Catalyzed Decyanative C–Se Cross-Coupling
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Traditionally, a metal-catalyzed cross-coupling reaction is governed by displacement of leaving groups such as halogens, tosylates, etc. by different nucleophiles leading to the formation of carbon-carbon and carbon-heteroatom bonds. Besides displacement of traditional leaving groups in coupling reactions decyanative cross-coupling has also received current attention. The objective of this work is to develop a decyanative cross-coupling through metal-assisted nucleophilic displacement, which is less explored so far. Thus, a decyanative cross-coupling of aryl selenocyanate with aryl-/alkylacetylenes, boronic acids and silanes has been accomplished by a copper-assisted nucleophilic displacement reaction for an easy access to a series of diaryl, aryl alkyl, aryl vinyl and aryl alkynyl selenides. The best yield of product was obtained using 5 mol% of Cu(OAc)2, Ag2CO3(20 mol%) and Cs2CO3(1 equiv.) at 100 °C for 8 h in N-methylpyrrolidinone (NMP). The advantages of simple operation, high yields and general applicability make this procedure more attractive. A mechanistic pathway has been proposed. Silver plays a key role in the decyanation process. A plausible mechanistic pathway of this decyanative carbon-selenium cross-coupling has been proposed based on UV, EPR, HR-MS and IR analytical data along with results obtained from control experiments. (Figure presented.).
- Mukherjee, Nirmalya,Kundu, Debasish,Ranu, Brindaban C.
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p. 329 - 338
(2017/02/05)
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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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- Organoselenium and DMAP co-catalysis: Regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes
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A catalytic system consisting of bis(4-methoxyphenyl)selenide and 4-(dimethylamino)pyridine (DMAP) has been developed for the regioselective synthesis of medium-sized bromo/iodo lactones and bromooxepanes possessing high transannular strain. 77Se NMR, mass spectrometry and theoretical studies reveal that the reaction proceeds via a quaternary selenium intermediate.
- Verma, Ajay,Jana, Sadhan,Prasad, Ch. Durga,Yadav, Abhimanyu,Kumar, Sangit
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supporting information
p. 4179 - 4182
(2016/03/19)
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- A Highly Efficient Copper-Catalyzed Synthesis of Unsymmetrical Diaryl- and Aryl Alkyl Chalcogenides from Aryl Iodides and Diorganyl Disulfides and Diselenides
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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
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supporting information
p. 777 - 781
(2016/03/12)
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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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supporting information
p. 11472 - 11476
(2016/11/28)
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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 0055; 0056
(2016/11/14)
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- Metal free synthesis of diaryl selenides using SeO2as a selenium source
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A simple, efficient, and eco-friendly synthetic protocol has been developed for the preparation of diaryl selenium compounds. To the best of our knowledge, this is the first Letter on the use of selenium dioxide as selenium source for the synthesis of diaryl selenides. Compared with other selenium sources the new source SeO2gives an environment-friendly and low-cost synthetic route, which may be useful for large-scale synthesis.
- Kumar, R. Uday,Reddy, K. Harsha Vardhan,Satish,Swapna,Nageswar
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supporting information
p. 4138 - 4141
(2016/08/24)
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- Diarylation of chalcogen elements using arylboronic acids via copper- or palladium-catalyzed oxidative coupling
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Transition metal-catalyzed diarylations of sulfur, selenium and tellurium were achieved using arylboronic acids in air. A copper-catalyzed reaction of sulfur or selenium efficiently yielded numerous symmetrical diaryl sulfides or selenides in the presence of NH4BF4. However, the diarylation of tellurium was not possible using this method, and required a palladium catalyst in the presence of KI and air for the reaction to proceed.
- Taniguchi, Nobukazu
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p. 5818 - 5823
(2016/08/30)
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- A highly efficient and reusable MCM-41-immobilized bipyridine copper(I) catalyst for the C-Se coupling of organoboronic acids with diaryl diselenides
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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
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p. 2106 - 2115
(2015/03/18)
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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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- Simple and catalyst-free method for the synthesis of diaryl selenides by reactions of arylselenols and arenediazonium salts
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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
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p. 1057 - 1061
(2014/02/14)
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- Recyclable 1,2-bis[3,5-bis(trifluoromethyl)phenyl]diselane-catalyzed oxidation of cyclohexene with H2O2: A practical access to trans-1,2-cyclohexanediol
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1,2-Bis[3,5-bis(trifluoromethyl)phenyl]diselane-catalyzed oxidation of cyclohexene by hydrogen peroxide affords a quick, clean and practical access to the important compound trans-1,2-cyclohexanediol under mild conditions. The highly atom-economic properties, clean procedures, high reaction concentration, short reaction time, mild conditions and eco-friendly, recyclable and low loading catalysts facilitate this methodology for possible future practical industrial production. Copyright
- Yu, Lei,Wang, Jun,Chen, Tian,Wang, Yuguang,Xu, Qing
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p. 652 - 656
(2014/08/05)
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- Simple and catalyst-free method for the synthesis of diaryl selenides by reactions of arylselenols and arenediazonium salts
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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
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p. 1057 - 1061
(2015/02/19)
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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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- The Chan-Lam reaction of chalcogen elements leading to aryl chalcogenides
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A copper-catalyzed chalcogenation of arylboronic acids with elemental sulfur or selenium is established, which provides diaryl disulfides or diaryl monoselenides in moderate to good yields with excellent selectivities, respectively. Moreover, after sequential reduction and coupling with aryl/alkyl iodides in one pot, unsymmetrical monosulfides were obtained in good yields.
- Yu, Jin-Tao,Guo, Huan,Yi, Yuanqiuqiang,Fei, Haiyang,Jiang, Yan
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supporting information
p. 749 - 752
(2014/04/03)
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- Investigations on the Lewis-acids-catalysed electrophilic aromatic substitution reactions of thionyl chloride and selenyl chloride, the substituent effects, and the reaction mechanisms
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The previously established aluminium-chloride-(AlCl3)-catalysed electrophilic aromatic substitution (EAS) of benzene (PhH) with thionyl chloride (SOCl2) has been extended to toluene (PhCH3), chlorobenzene (PhCl), and phenol (PhOH). -CH3 was found to be mainly a para-director with a minor ortho-directing effect on the EAS reactions giving diaryl sulfoxides (Ar2SO). -Cl was found to be exclusively a para-director for formation of Ar2SO. All the -CH3, -Cl, and -OH groups were shown to be exclusive para-directors for formation of diaryl sulfides (Ar2S) from the EAS reactions. Although the reactions of PhH and PhCH3 with SOCl2 in the presence of AlCl 3 gave the major Ar2SO and minor Ar2S at ambient temperature, the phenol (PhOH) reaction was shown to give only the reduced sulfide (p-HOC6H4)2S with no sulfoxide (p-HOC6H4)2SO formed. The mixed diaryl sulfoxides ArSOAr′ (Ar, Ar′=C6H5, p-CH 3C6H4; C6H5, o-CH 3C6H4; and C6H5, p-ClC6H4) were produced in the AlCl3-catalysed reactions of SOCl2 with molar 1:1 PhH-PhX mixtures (X=CH3 and Cl). Efforts to enhance the yield of S-aryl arenesulfonothioates ArSO 2SAr (Ar=Ph, p-CH3C6H4, and p-ClC6H4) from the AlCl3-catalysed EAS reactions of SOCl2 were made, showing that decreasing the molar ratios of ArH/SOCl2 or lowering the temperature resulted in an increase in the product yield. A detailed mechanism has been proposed to account for the formation of ArSO2SAr. The Lewis-acid-MCl3-(M=Al and Fe)-catalysed EAS reactions of PhH with selenyl chloride (SeOCl2) were demonstrated to give the reduced diphenyl selenide (Ph2Se) and diphenyl diselenide (PhSeSePh) via novel auto-redox processes in selenium of the key EAS intermediates.
- Sun, Xiaoping,Haas, David,McWilliams, Samantha,Smith, Benjamin,Leaptrot, Katrina
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p. 736 - 744
(2014/01/23)
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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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- Potassium tert-butoxide-mediated synthesis of unsymmetrical diaryl ethers, sulfides and selenides from aryl bromides
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Potassium tert-butoxide mediated carbon-chalcogen C-E (E=O, S and Se) coupling reaction has been studied from aryl bromide and phenol/aryl disulfide/diselenide substrates. A series of unsymmetrical diaryl chalcogenides were accessed from aryl bromide and diaryl dichalcogenide precursors by using 2.5 equiv of potassium tert-butoxide in DMSO at 80 C. Unsymmetrical diaryl ethers were also obtained by using phenol precursors at 40-45 C. Aryl bromides with methyl, trifluoromethyl, methoxy and nitro substituents showed compatibility in the carbon-chalcogen bond forming reaction. 4-Methoxy, methyl, trifluoromethyl substituted bromobenzene substrates gave two regioisomers: 3-substituted and 4-substituted diaryl chalcogenides when reacted with phenols/diaryl disulfides/diselenides. Formation of two regioisomeric diaryl chalcogenides in the reaction mixture suggests that potassium tert-butoxide reacts with bromobenzene to produce benzyne intermediate, which subsequently reacts with diaryl dichalcogenides and finally give a regioisomeric mixture of 4-substituted and 3-substituted diaryl chalcogenides.
- Kumar, Amit,Bhakuni, Bhagat Singh,Prasad, Ch. Durga,Kumar, Shailesh,Kumar, Sangit
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p. 5383 - 5392
(2013/07/04)
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- Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides
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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
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p. 1141 - 1147
(2013/07/26)
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- An efficient one-pot approach to selenides: CuI-catalyzed reactions of magnesium selenolate with aryl or alkyl halides
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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
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p. 787 - 793
(2013/07/26)
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- A general and green procedure for the synthesis of organochalcogenides by CuFe2O4 nanoparticle catalysed coupling of organoboronic acids and dichalcogenides in PEG-400
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A general and efficient procedure has been developed for the synthesis of organochalcogenides (selenides and tellurides) by a simple reaction of organoboronic acids and dichalcogenides catalysed by CuFe2O 4 nanoparticles in PEG-400 without any ligand. This protocol offers the scope for access to a wide spectrum of chalcogenides including diaryl, aryl-heteroaryl, aryl-styrenyl, aryl-alkenyl, aryl-allyl, aryl-alkyl and aryl-alkynyl versions. The catalyst is magnetically separable and recyclable eight times without any loss of appreciable catalytic activity. The products are obtained in high purities after evaporation of solvent followed by filtration column chromatography. The Royal Society of Chemistry.
- Kundu, Debasish,Mukherjee, Nirmalya,Ranu, Brindaban C.
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p. 117 - 125
(2013/04/10)
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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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