- Rongalite-Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides
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The on water reaction of sodium telluride with electrophiles has been explored. Na2Te, generated in situ through the rongalite (sodium hydroxymethanesulfinate)-promoted reduction of elemental tellurium, reacts with a wide variety of electrophil
- Capperucci, Antonella,Ricci, Lorenzo,Tanini, Damiano
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- Reaction of arylhydrazines with diaryl ditellurides in the air: Insight into bimolecular homolytic substitution on tellurium via Aryl–Te bond cleavage
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The reactivity of diaryl ditelluride and diaryl telluride toward aryl radicals was studied in detail. Diphenyl ditelluride underwent a bimolecular homolytic substitution (SH2) reaction with a phenyl radical generated from phenylhydrazine in the air, to afford diphenyl telluride in excellent yield. Based on this diphenyl telluride synthesis, a one-pot synthesis of unsymmetrical diaryl tellurides was developed by the SH2 reaction of in situ generated diphenyl telluride with arylhydrazines in the air. The selectivity of mono-/di-substitution and the reactivity of arylhydrazines depend on the nature of the substituents on the arylhydrazines, that is, electron-donating or -withdrawing group.
- Yamamoto, Yuki,Sato, Fumiya,Kodama, Shintaro,Nomoto, Akihiro,Ogawa, Akiya
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- Facile one-step synthesis of palladium tellurium alloy nanorods
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A palladium-tellurium binary alloy nanomaterial was synthesized by a one-pot reaction of bis(4-methoxyphenyltelluro)methane [(4-CH3O-C6H4Te)2CH2](1) and allylpalladium (II)chloride dimer [(η3-C3H5)2Pd2(μ-Cl2)] (2) in 1:1 ratio using methylene chloride as solvent at ambient conditions. In addition to the Pd20Te7 alloy nanomaterial (3) generated, a palliadum (II) tellurolate complex [PdC1(μ-TeC6H4-OCH3)Te(C6H4-OCH3)2]2 (6), and other organic and organotellurim compounds were isolated as byproducts using column chromatography. The palladium-tellurium binary alloy nanomaterial and other byproducts from the reaction were characterized by powder X-ray diffraction (PXRD), NMR, GC-MS, transmission electron microscopy (TEM), and single crystal X-ray diffractions (XRD) methods. The palladium-tellurium binary alloy nanomaterial was obtained as single-phase Pd20Te7 nanorods, under mild conditions. TEM results indicated that the nanorods are less than 15 nm in diameter and range from 40 to 200 nm in length. A nanomaterial mixture was isolated with two binary-phases Pd20Te7 and Pd10Te3 when benzene was used as solvent. Compound 6 was successfully tested for catalytic activity for the Heck Reaction and produced a mixture of PdTe2 with Pd13Te3 nanomaterials as byproducts.
- Mariappan, Kadarkaraisamy,Varapragasam, Shelton J.P.,Hansen, Matthew R.,Rasalingam, Shivatharsiny,Alaparthi, Madhubabu,Sykes, Andrew G.
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p. 251 - 256
(2018/05/23)
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- Synthesis of symmetrical and unsymmetrical tellurides via silver catalysis
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We describe here a simple and efficient methodology for the cross-coupling reaction of diaryl ditellurides with aryl boronic acids catalyzed by AgNO3. The general applicability and wide substrate scope make this an interesting method for the synthesis of a series of symmetrical and unsymmetrical diaryl tellurides. This silver-catalyzed protocol tolerates a variety of diaryl ditellurides as well as aryl boronic acids by using only 10 mol% of AgNO3 to provide the desired products in high yields. The reaction mechanism was proposed after high resolution mass spectrometry analysis and the active (PhTe)2AgIII intermediate could be detected.
- Goldani, Bruna,do Sacramento, Manoela,Lenard?o, Eder J.,Schumacher, Ricardo F.,Barcellos, Thiago,Alves, Diego
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supporting information
p. 15603 - 15609
(2018/10/04)
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- Carbon-carbon bond forming reactions via Pd-catalyzed detellurative homocoupling of diorganyl tellurides
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A simple and highly efficient method for the constructions of Csp-Csp, Csp2-Csp2 and Csp3-Csp3 bonds is reported. The symmetrical diaryl tellurides undergo detellurative homocouplings to afford symmetrical biaryl products. The reactions are carried out at ambient temperature using PdCl2 as a catalyst in the presence of Ag2O and Na2CO3. Similarly, the detellurative homocouplings of dibenzyl telluride and bis(phenylethynyl)telluride give bibenzyl and the conjugated diyne, respectively.
- Zhang, Shaozhong,Kolluru, Lalitha,Vedula, Souseelya K.,Whippie, Drew,Jin, Jin
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supporting information
p. 3594 - 3597
(2017/08/23)
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- The Anticancer Activity of Organotelluranes: Potential Role in Integrin Inactivation
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Organic TeIV compounds (organotelluranes) differing in their labile ligands exhibited anti-integrin activities in vitro and anti-metastatic properties in vivo. They underwent ligand substitution with l-cysteine, as a thiol model compound. Unlike inorganic TeIV compounds, the organotelluranes did not form a stable complex with cysteine, but rather immediately oxidized it. The organotelluranes inhibited integrin functions, such as adhesion, migration, and metalloproteinase secretion mediation in B16F10 murine melanoma cells. In comparison, a reduced derivative with no labile ligand inhibited adhesion of B16F10 cells to a significantly lower extent, thus pointing to the importance of the labile ligands of the TeIV atom. One of the organotelluranes inhibited circulating cancer cells in vivo, possibly by integrin inhibition. Our results extend the current knowledge on the reactivity and mechanism of organotelluranes with different labile ligands and highlight their clinical potential.
- Silberman, Alon,Kalechman, Yona,Hirsch, Shira,Erlich, Ziv,Sredni, Benjamin,Albeck, Amnon
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p. 918 - 927
(2016/05/24)
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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 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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- Catalyst free one-pot synthesis of symmetrical diaryl tellurides with Te0/KOH
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A highly efficient new protocol for C-Te bond formation leading to symmetrical diaryl tellurides has been developed. The synthesis employed aryl iodides and elemental tellurium as starting materials in the presence of KOH. It is a one-pot reaction without using any catalyst. Utilizing this new protocol, a variety of aryl and heteroaryl iodides are reacted with elemental tellurium to afford the corresponding diaryl tellurides in good to excellent yields.
- Zhang, Shaozhong,Karra, Kranthi,Koe, Adam,Jin, Jin
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supporting information
p. 2452 - 2454
(2013/06/05)
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- An alternative approach for the synthesis of aryl-alkyl tellurides: Reaction of aryl iodides with metal alkyltellurolates promoted by CuI
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Aryl iodides react with metal organotellurolates in tetrahydrofuran/ dimethylformamide in the presence of CuI (5 mol %) or CuI (5 mol %) and 1,10-phenanthroline (10 mol %) to afford the corresponding aryl-alkyl tellurides in good yields.
- Silva, Márcio S.,Comasseto, Jo?o V.
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supporting information; experimental part
p. 8763 - 8768
(2011/12/02)
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- Negishi cross-coupling of organotellurium compounds: Synthesis of biaryls, aryl-, and diaryl acetylenes
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A functional group tolerant palladium-catalyzed Negishi coupling of diaryl tellurides with organozinc has been developed. This methodology permits efficient preparation of biaryls, aryl acetylenes and diaryl acetylenes in moderate to good yields. A preliminary study to gain further insight into the reaction was performed using in situ ReactIR technology.
- Stefani, Helio A.,Pena, Jesus M.,Manarin, Flavia,Ando, Romulo A.,Leal, Daiana M.,Petragnani, Nicola
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supporting information; experimental part
p. 4398 - 4401
(2011/09/19)
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- Aerobic photooxidation of phosphite esters using diorganotelluride catalysts
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Diorganotellurides containing bulky aromatic substituents are found to catalyze the photooxidation of phosphite esters using aerobic oxygen as a terminal oxidant. A Hammett plot with substituted triaryl phosphites yielding p = 2.88 agrees with a nucleophilic oxygen transfer from telluroxide to phosphite.2009 American Chemical Society.
- Oba, Makoto,Okada, Yasunori,Nishiyama, Kozaburo,Ando, Wataru
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supporting information; experimental part
p. 1879 - 1881
(2009/10/10)
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- Deoxygenation of sulfoxides, selenoxides, telluroxides, sulfones, selenones and tellurones with Mg-MeOH
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The deoxygenation of a variety of sulfoxides, selenoxides, telluroxides, sulfones, selenones and tellurones has been reported with Mg-MeOH at room temperature in nearly quantitative yields. The deoxygenation is proposed to proceed by SET from Mg to the substrate.
- Khurana, Jitender M.,Sharma, Vandana,Chacko, Silvi A.
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p. 966 - 969
(2007/10/03)
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- Mild reduction of tellurium(IV) and selenium(IV) compounds by sodium ascorbate
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Sodium ascorbate was found to mildly reduce organyltellurium trihalides to diorganyl ditellurides, organylselenium trihalides to diorganyl diselenides, diorganyltellurium dihalides and oxides to diorganyl tellurides and diorganylselenium dihalides and oxides to diorganyl selenides.
- Engman,Persson
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p. 445 - 458
(2007/10/02)
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- Synthesis and characterization of dimethyl- and dimethoxyphenylbis(N,N-dialkyldithiocarbamato)tellurium(IV) and chlorodimethyl- and chlorodimethoxyphenyl-(N,N-dialkyldithiocarbamato)tellurium(IV). Crystal structures of Me2Te2 and (p-MeOC6H4)2Te2
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The compounds Me2Te2, Me2TeCl, (p-MeOC6H4)2Te2, and (p-MeOC6H4)2TeCl, where R = Me, Et, have been prepared and characterised primarily by vibrational and NMR spectroscopy.Variable temperature NMR spectroscopy and qualitative time studies indicate that in solution the dimethoxyphenyltellurium derivatives undergo the reductive-elimination noted for analogous phenyl derivatives but the reductive-elimination does not occur with the dimethyl tellurium derivatives.The crystal structures of Me2Te2, 1, and (p-MeOC6H4)2Te2, 5, were completed.The cell parameters for 1, which crystallizes as monoclinic in space group P21/n, are a = 13.550(2), b = 13.034(2), c = 17.854(2) Angstroem, β = 106.61(1) deg, V = 3021.6(7) Angstroem3, Z = 8, R = 0.0368, and Rw = 0.0402 and for 5, which crystallizes as monoclinic in space group C2/c, are a = 35.36(1), b = 11.063(3), c = 12.778(3) Angstroem, β = 96.16(3) deg, V = 4963(3) Angstroem3, Z = 8, R = 0.0627, and Rw = 0.0646.
- Bailey, Jane H. E.,Drake, John E.
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- Convenient synthesis of diaryl tellurides
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Diaryl tellurides 5 are prepared by two synthetic routes: a) a one-pot procedure using elemental tellurium (1), diethyl phosphite (2) and sodium hydride in ethanol, followed by treatment with arenediazonium fluoroborates 4; b) treatment of sodium telluride (6) with arenediazonium fluoroborates 4 in dimethylformamide. In both cases, good yields are obtained.
- Li,Lue,Zhou
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p. 281 - 283
(2007/10/02)
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- Hypervalent iodine in synthesis. VI. The electrophilic arylation of diaryliodonium salts to sodium telluride
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Diaryliodonium salts readily take place electrophilic arylation at Te to afford symmetrical diaryl tellurides in good yields.
- You,Chen
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p. 1441 - 1444
(2007/10/02)
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- Sodium telluride in N-methyl-2-pyrrolidone: An efficient telluration system for the synthesis of aromatic tellurides and ditellurides
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Sodium telluride prepared in situ from tellurium and sodium hydride in N-methyl-2-pyrrolidone was found to act as an efficient tellurating agent for nonactivated aromatic iodides, providing a simple route to a variety of diaryl tellurides, alkyl aryl tellurides and diaryl ditellurides.
- Suzuki,Nakamura
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p. 549 - 551
(2007/10/02)
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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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p. 1729 - 1734
(2007/10/02)
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- SYNTHESIS, STRUCTURE, AND PROPERTIES OF COMPOUNDS WITH A CHALCOGEN-NITROGEN BOND XIII. THE EFFECT OF THE NATURE OF THE CHALCOGEN ATOM ON THE ABILITY OF N-SULFONYLCHALCOGENIMIDES TO OXIDIZE HYDROQUINONE AND ITS DERIVATIVES
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N-Sulfonyldiphenylsulfimides do not react with hydroquinone, 2,5-di(tert-butyl)hydroquinone, and tetrahydroxy-p-benzoquinone even with prolonged heating above 150 deg C.Selenimides and tellurimides with analogous structures oxidize these compounds to the corresponding quinones.The oxidizing power of the tellurimides in the investigated reations is higher than that of the selenimides.This is explained by the increased polarity of the chalcogen-nitrogen bond and, consequently, the ease of its cleavage in N-sulfonylchalcogenimides in the series: S Se Te.The intermediate products from the reaction of the tellurium derivatives with hydroquinone, i.e., polymeric diaryltellurium p-hydroxyphenolates, were isolated.
- Naddaka, V. I.,Avanesyan, K. V.,Cherkinskaya, M. L.
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p. 705 - 711
(2007/10/02)
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- SYNTHESIS, STRUCTURE, AND PROPERTIES OF COMPOUNDS WITH A CHALCOGEN-NITROGEN BOND. X. REACTION OF TELLURIMIDES WITH THIOLS AND THIOAMIDES
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Tellurimides readily oxidize thiophenol and benzyl hydrogen sulfide at room temperature to the corresponding disulfides, thiourea to cyanamide, thiobenzamide to benzonitrile, and 1,3-diphenylthiourea to diphenylcarbodiimide.
- Naddaka, V. I.,Avenesyan, K. V.,Cherkinskaya, M. L.,Minkin, V. I.
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p. 1426 - 1429
(2007/10/02)
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- Co2(CO)8-mediated and -catalyzed carbonylation of diaryl diselenides and ditellurides to seleno and telluro esters
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Diaryl diselenides and ditellurides react with CO (5-100 atm) at 100-200 deg C in the presence of Co2(CO)8 to give the corresponding seleno and telluro esters in 21-96percent yield.The carbonylation proceeds catalytically in Co2(CO)8 in the presence of triphenylphosphine.It was shown unambiguously that benzoylcobalt tetracarbonyl, which is one of possible intermediates, reacts with diphenyl diselenide or ditelluride to give phenyl selenobenzoate or tellurobenzoate, respectively.
- Takahashi, Hidetaka,Ohe, Kouichi,Uemura, Sakae,Sugita, Nobuyuki
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p. C43 - C45
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF SYMMETRICAL DIARYL TELLURIDES USING TELLURIUM/RONGALITE AS TELLURATION SYSTEM
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Sodium telluride, prepared by reducing tellurium with rongalite in dilute aqueous sodium hydroxide, readily reacts with nonactivated aryl iodides to afford symmetrical diaryl tellurides in good yields.
- Suzuki, Hitomi,Inouye, Masahiko
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p. 389 - 390
(2007/10/02)
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- Oxidation process using tellurium oxide catalysts
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The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C=S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: STR1 wherein R and R1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.
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- New General Synthesis of Diaryl Tellurides from Aromatic Amines
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A number of substituted diaryl tellurides were obtained from aryldiazonium tetrafluoroborates and potassium tellurocyanide in dimethyl sulfoxide at ambient temperature.Aryl tellurocyanides were isolated as byproducts in some experiments and postulated as
- Engman, Lars
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p. 2920 - 2922
(2007/10/02)
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- Synthesis and Reactions of Bis(p-methoxyphenyl)tellurone
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Bis(p-methoxyphenyl)tellurone, the first definitely characterized tellurone, has been prepared by periodate oxidation of the corresponding telluroxide and its oxidizing properties have been studied.
- Engman, Lars,Cava, Michael P.
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p. 164 - 165
(2007/10/02)
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- Synthesis of 2,5-dihydrotellurophene - A new heterocyclic compound
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2,5-Dihydrotellurophene 1,1-dichloride was isolated in 62% yield when TeCl4 was heated in acetonitrile with an excess of butadiene. Isoprene and 2,3-dimethylbutadiene reacted similarly affording the 3-methyl- and the 3,4-dimethyl-substituted 2,5-dihydrotellurophene 1,1-dichlorides which were easily reduced with aqueous Na2S to the corresponding 2,5-dihydrotellurophenes. 2,5-Dihydrotellurophene could be converted to its 1,1-dibromide and 1,1-diiodide, respectively, by treatment with Br2 and I2. Treatment with XeF2 afforded the 1,1-difluoride and oxidation with H2O2 similarly afforded 2,5-dihydrotellurophene 1-oxide, which was not isolated. The double bond of 2,5-dihydrotellurophene 1,1-dichloride was inert to treatment with Br2 or Cl2, probably due to an interaction, either steric or electronic, with the TeCl2 group.
- Bergman, Jan,Engman, Lars
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p. 2715 - 2718
(2007/10/20)
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- SYNTHESIS AND STRUCTURE OF AROMATIC AND HETEROCYCLIC COMPOUNDS OF TELLURIUM. XVIII. ABNORMAL THERMAL DISSOCIATION OF 2-DIORGANOTELLURIODIMEDONIDES
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When 2-diorganotelluroniodimedonides are boiled in o-xylene cleavage of the ylide bond occurs, and the corresponding tellurides and the trimer of the carbanionic fragment, which is a derivative of the tetrahydrofuro-1,3-dioxepin system, are formed.
- Sadekov, I. D.,Usachev, A. I.,Minkin, V. I.
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p. 919 - 921
(2007/10/02)
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