- 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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- 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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- 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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- 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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- Synthesis of Unsymmetrical Diaryl Selenides: Copper-Catalyzed Se-Arylation of Diaryl Diselenides with Triarylbismuthanes
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Copper-catalyzed C(aryl)-Se bond formation by the reaction of diaryl diselenides with triarylbismuthanes in the presence of copper(I) acetate (10 mol%) and 1,10-phenanthroline (10 mol%) under aerobic conditions led to the formation of unsymmetric diaryl s
- Matsumura, Mio,Shibata, Kohki,Ozeki, Sota,Yamada, Mizuki,Murata, Yuki,Kakusawa, Naoki,Yasuike, Shuji
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p. 730 - 736
(2016/03/01)
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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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- 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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- 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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- Reduction of diaryltellurium dichlorides with samarium diiodide
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Samarium diiodide reduces diaryltellurium dichlorides to the corresponding diaryl tellurides in moderate to good yields under mild and neutral conditions.
- Jia,Zhang,Zhou
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p. 253 - 258
(2007/10/02)
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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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- 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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- 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 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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- Mechanism of Thermal Decomposition of Tetra-aryltellurium Species
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Tetra-aryltellurium species decompose upon heating giving good yields of diaryl tellurides and biphenyls.Radical-scavenging experiments show that phenyl radicals are not intermediates in the formation of biphenyls.In contrast, cross-over experiments give mixed biphenyls as well as mixed diaryl tellurides, but these are formed by a statistical redistribution of organic groups giving mixed tetra-aryltellurium species which decompose thermally in an indiscrimate fashion.
- Glover, Stephen A.
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p. 1338 - 1344
(2007/10/02)
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- Tellurium in Organic Synthesis, IX Oxidation of Some Nitrogenous Compounds with TeO2
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Some phenylhydrazines were readily converted to diaryltellurium dichlorides in 27-40percent yield when treated with TeO2 in refluxing acetic acid containing lithium chloride.It was also found that certain ketones could be regenerated from their corresponding semicarbazones, azines and hydrazones when submitted to the same reaction conditions. - Keywords: Tellurium, Phenylhydrazines
- Bergman, Jan,Engman, Lars
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p. 882 - 884
(2007/10/02)
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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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