substitution (SH2) reaction between the aryl radical and diaryl ditelluride. Aryl radicals are generated from arylhydrazines in air and captured by diaryl ditellurides, resulting in a selective formation of unsymmetrical diaryl tellurides with high yields. The electronic effects of the substituents on both arylhydrazines and diaryl ditellurides on the SH2 reaction of tellurium are also discussed in detail.
We report the Lewis acid catalysis of aryldiazoniumsalts, and their Lewis acidity applications in photogeneration of aryl radicals under additive-, photocatalyst- and transition metal-free conditions. In this visible light-mediated transformation, the Lewis acidic character of aryldiazoniumsalts enables access to the photoactive charge transfer complex with dichalcogenides. The usefulness and versatility
Visible Light Photocatalyzed Direct Conversion of Aryl-/Heteroarylamines to Selenides at Room Temperature
作者:Debasish Kundu、Sabir Ahammed、Brindaban C. Ranu
DOI:10.1021/ol500567t
日期:2014.3.21
A novel strategy for the direct conversion of aryl- and heteroarylamines to selenides has been developed via diazotization of amines with tert-butyl nitrite in neutral medium followed by reaction with diaryl/diheteroaryl/dialkyl diselenides in one pot under photocatalysis at room temperature in the absence of any metal. This reaction is also applied for the synthesis of tellurides. The selenylation of heteroarylamine by this protocol is of much significance because of the difficulty in diazotization of these molecules by a standard diazotization method in acid medium.
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.
Reaction under Ball-Milling: Solvent-, Ligand-, and Metal-Free Synthesis of Unsymmetrical Diaryl Chalcogenides
作者:Nirmalya Mukherjee、Tanmay Chatterjee、Brindaban C. Ranu
DOI:10.1021/jo402071b
日期:2013.11.1
A convenient, efficient, and general procedure for the synthesis of diaryl chalcogenides including sulfides, selenides and tellurides has been developed by the reaction of diazonium tetrafluoroborates and diaryl dichalcogenides on the surface of alumina under ball-milling without any solvent or metal. A wide range of functionalized diaryl chalcogenides are obtained in high purity by this procedure.