Two sets of cascade processes have been realized, both of which were initiated with a benzyne insertion into the Se═O bond. The key factors to differentiate these processes are based on the structures of diaryl selenium oxides and reaction conditions. When diaryl selenium oxides containing an weak σ-electron-withdrawing group were used, triarylselenonium salts were obtained at room temperature, while -(aryloxy)phenyl phenyl selanes could be produced from diaryl selenium oxides at 100 °C.
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http://dx.doi.org/10.1021/acs.orglett.3c00304 | DOI Listing |
Org Lett
January 2025
School of Chemistry & Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China.
The translocation of an aryl group from selenium into carbon enabled by the cleavage of the C-Se bond is reported by using nitrogen atom-linked 1,7-diynes and diaryl diselenides as starting materials, leading to various selenophene derivatives in a regioselective manner. This method enables the construction of two C-Se bonds and two C-C bonds through sequential radical bicyclization and 1,2-aryl migration under metal-free conditions. Control experiments and mechanistic studies suggest that this reaction proceeds through the cleavage of the inert C(Ph)-Se bond, facilitating the aryl translocation process.
View Article and Find Full Text PDFFront Chem
December 2024
Department of Chemistry, Cleveland State University, Cleveland, OH, United States.
Quenching peroxynitrite (a reactive oxidant species) is a vital process in biological systems and environmental chemistry as it maintains redox balance and mitigates damaging effects in living cells and the environment. In this study, we report a systematic analysis of the mechanism of transforming peroxynitrite into nitrate using diaryl selenide in water. Through quantum mechanical calculations, we investigate the dynamic isomerization of peroxynitrite in a homogeneous catalytic environment.
View Article and Find Full Text PDFActa Trop
October 2024
Laboratory of Veterinary Clinical Parasitology, Department of Veterinary Medicine, Federal University of Paraná, Curitiba, Paraná 80035-050, Brazil. Electronic address:
Fasciolosis is a food and waterborne disease caused by Fasciola spp., representing a global health burden to various hosts, including humans and other animals. This study investigates the in vitro activity of tellurium- and selenium-containing diaryl dichalcogenides: diacetal ditelluride (LQ07), diacetal diselenide (LQ62), and diacetyl diselenide (LQ68) alone and in combination with ivermectin (IVM) against eggs of Fasciola hepatica.
View Article and Find Full Text PDFJ Org Chem
August 2024
CNRS, Bordeaux INP, ISM, UMR 5255, University of Bordeaux, F-33400 Talence, France.
The in situ base-promoted generation of unstable selenophenolate anions from 1,2-benzisoselenazoles via a variant of the Kemp elimination has been developed. 2-Cyano-substituted selenophenolate anions obtained by this methodology were engaged in nucleophilic substitution, aromatic nucleophilic substitution, and Pd-catalyzed cross-coupling reactions to give functionalized arylalkyl and diaryl selenides in moderate to excellent yields.
View Article and Find Full Text PDFBeilstein J Org Chem
May 2024
Department of Chemistry, School of Advanced Sciences, VIT-AP University, Amaravati-522237, Andhra Pradesh, India.
This article describes the detailed analysis of the reaction between arylamines, such as aniline, -anisidine, and methyl anthranilate, with selenium dioxide in acetonitrile. A systematic analysis of the reaction products with the help of Se NMR and single-crystal X-ray crystallography revealed that the reaction progress follows three major reaction pathways, electrophilic selenation, oxidative polymerization, and solvent oxidation. For aniline and -anisidine, predominant oxidative polymerization occurred, leading to the formation of the respective polyaniline polymers as major products.
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