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
Synthesis of Unsymmetrical Diorganyl Chalcogenides under Greener Conditions: Use of an Iodine/DMSO System, Solvent- and Metal-Free Approach
作者:Sumbal Saba、Jamal Rafique、Antonio L. Braga
DOI:10.1002/adsc.201500024
日期:2015.5.4
Herein, we report a greeneriodine‐catalyzed protocol to access different types of unsymmetricaldiorganylchalcogenides. 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
When heated in hexamethylphosphoric triamide at 80–90°C, preferably in the presence of copper(I) iodide, moderately activated iodoarenes undergo nucleophilic attack by benzenetellurolate ion, giving the corresponding unsymmetrical diaryl tellurides in fair to good yields.
Solvent selective phenyl selenylation and phenyl tellurylation of aryl boronic acids catalyzed by Cu(II) grafted functionalized polystyrene
作者:Susmita Roy、Tanmay Chatterjee、Sk. Manirul Islam
DOI:10.1016/j.tetlet.2014.12.055
日期:2015.2
A solvent-selective methodology for the phenyl selenylation and phenyl tellurylation of aryl boronic acids has been developed for the first time using a polymer supported Cu(II) catalyst. The catalyst was synthesized by anchoring Cu(OAc)(2) onto a functionalized polystyrene with pyridine thiosemicarbazone ligand. It was then characterized properly by SEM, EDAX, FT-IR, TGA, and EPR experiments. The catalyst smoothly catalyzes phenyl selenylation of aryl boronic acids in water and phenyl tellurylation of aryl boronic acids in PEG-600, selectively. Thus a wide variety of unsymmetrical organodiaryl or aryl-heteroaryl selenides and tellurides have been synthesized by this protocol. The catalyst was recycled up to six runs without any appreciable loss of catalytic activity. (C) 2014 Elsevier Ltd. All rights reserved.
A convenient and efficient copper-catalyzed synthesis of unsymmetrical and symmetrical diaryl chalcogenides from arylboronic acids in ethanol at room temperature
作者:Amit Kumar、Sangit Kumar
DOI:10.1016/j.tet.2014.01.030
日期:2014.3
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 NaBH4 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. (C) 2014 Elsevier Ltd. All rights reserved.