56949-99-6Relevant academic research and scientific papers
Trichloroisocyanuric Acid-Promoted Synthesis of Arylselenides and Aryltellurides from Diorganyl Dichalcogenides and Arylboronic Acids at Ambient Temperature
Sun, Nan,Zheng, Kai,Sun, Pengyuan,Chen, Yang,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
, p. 3577 - 3584 (2021/06/15)
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.).
Metal-Free Synthesis of Unsymmetrical Aryl Selenides and Tellurides via Visible Light-Driven Activation of Arylazo Sulfones
Fagnoni, Maurizio,Li, Ankun,Li, Yuxuan,Liu, Junjie,Lu, Kui,Protti, Stefano,Shan, Xiwen,Tian, Miaomiao,Zhao, Xia
supporting information, p. 7358 - 7367 (2020/12/01)
A protocol for the visible light driven preparation of unsymmetrical (hetero)aryl selenides and tellurides is described herein. The method exploits the peculiar photoreactivity of arylazo sulfones that act as thermally stable, precursors of aryl radicals under both photocatalyst- and additive-free conditions. The method developed shows an impressive versatility (more than fifty compounds isolated).
C-Te Cross-Coupling of Diaryl Ditellurides with Arylboronic Acids by Using Copper(I) Thiophene-2-carboxylate under Mild Conditions
Koguchi, Shinichi,Shibuya, Yuga,Igarashi, Yusuke,Takemura, Haruka
, p. 99 - 103 (2019/01/04)
We describe the successful cross-coupling of diaryl ditellurides with arylboronic acids by using copper(I) thiophene-2-carboxylate (CuTC) under mild conditions. Although other studies have reported that highly polar solvents (such as DMSO) or bases are required, this reaction was completed by using CuTC and common solvents under neutral conditions at room temperature. This cross-coupling reaction was performed with diaryl ditellurides and arylboronic acids bearing various groups, affording the corresponding diaryl tellurides in good to excellent yields.
Synthesis of symmetrical and unsymmetrical tellurides via silver catalysis
Goldani, Bruna,do Sacramento, Manoela,Lenard?o, Eder J.,Schumacher, Ricardo F.,Barcellos, Thiago,Alves, Diego
supporting information, p. 15603 - 15609 (2018/10/04)
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.
Alternative Metal-Free Synthesis of Diorganoyl Selenides and Tellurides Mediated by Oxone
Perin, Gelson,Duarte, Luis Fernando B.,Neto, José S. S.,Silva, Márcio S.,Alves, Diego
supporting information, p. 1479 - 1484 (2018/05/03)
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.
Reaction of arylhydrazines with diaryl ditellurides in the air: Insight into bimolecular homolytic substitution on tellurium via Aryl–Te bond cleavage
Yamamoto, Yuki,Sato, Fumiya,Kodama, Shintaro,Nomoto, Akihiro,Ogawa, Akiya
, (2019/01/09)
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.
Copper-catalyzed synthesis of unsymmetrical diorganyl chalcogenides (Te/Se/S) from boronic acids under solvent-free conditions?
Saba, Sumbal,Botteselle, Giancarlo Vaccari,Godoi, Marcelo,Frizon, Tiago Elias Allievi,Galetto, Fábio Zazyki,Rafique, Jamal,Braga, Antonio L.
, (2017/08/29)
The efficient and mild copper-catalyzed synthesis of unsymmetrical diorganyl chalcogenides under ligand- and solvent-free conditions is described. The cross-coupling reaction was performed using aryl boric acids and 0.5 equiv. of diorganyl dichalcogenides (Te/Se/S) in the presence of 3 mol % of CuI and 3 equiv. of DMSO, under microwave irradiation. This new protocol allowed the preparation of several unsymmetrical diorganyl chalcogenides in good to excellent yields.
Carbon-carbon bond forming reactions via Pd-catalyzed detellurative homocoupling of diorganyl tellurides
Zhang, Shaozhong,Kolluru, Lalitha,Vedula, Souseelya K.,Whippie, Drew,Jin, Jin
, p. 3594 - 3597 (2017/08/23)
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.
Iron(0) nanoparticles mediated direct conversion of aryl/heteroaryl amines to chalcogenides via in situ diazotization
Panja, Subir,Maity, Pintu,Kundu, Debasish,Ranu, Brindaban C.
supporting information, p. 3441 - 3445 (2017/08/10)
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.
Synthesis of unsymmetrical diorganyl chalcogenides under greener conditions: Use of an iodine/DMSO system, solvent- and metal-free approach
Saba, Sumbal,Rafique, Jamal,Braga, Antonio L.
supporting information, p. 1446 - 1452 (2015/05/27)
Herein, we report a greener iodine-catalyzed protocol to access different types of unsymmetrical diorganyl chalcogenides. This new approach works in the absence of solvent and metal. The desired products were obtained in good to excellent yields using one equivalent of arylboronic acids, half an equivalent of various diorganyl dichalcogenides, iodine (10 mol%) as a catalyst and 2 equivalents of dimethyl sulfoxide (DMSO; as oxidant), with a reaction time of 10 min under microwave irradiation.
