{"title":"Direct C–H selenylation of (Benz)imidazole and related heterocycles via cooperative action of palladium and silver catalyst","authors":"Pranali Prabhakar Thakur, Manali Pawar, Mahendra Patil","doi":"10.1016/j.tet.2025.134667","DOIUrl":null,"url":null,"abstract":"<div><div>The selenylation of (benz)imidazole and related heteroarenes has been successfully achieved using PdCl<sub>2</sub>/Ag<sub>2</sub>O/Xantphos as a catalytic system. This method exploits the cooperative action of palladium and silver catalyst to activate diaryl diselenides as well as C–H bonds of (benz)imidazole and related heteroarenes, enabling the effective coupling of selenium moieties with these heteroarenes. Control experiments involving variation in catalyst loading revealed the synergistic interaction between Pd and Ag catalyst in the reaction. The unification of these robust catalytic systems ensures optimal outcome in the synthesis of a diverse array of organoselenium compounds featuring aryl-heteroaryl scaffolds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134667"},"PeriodicalIF":2.1000,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402025002236","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The selenylation of (benz)imidazole and related heteroarenes has been successfully achieved using PdCl2/Ag2O/Xantphos as a catalytic system. This method exploits the cooperative action of palladium and silver catalyst to activate diaryl diselenides as well as C–H bonds of (benz)imidazole and related heteroarenes, enabling the effective coupling of selenium moieties with these heteroarenes. Control experiments involving variation in catalyst loading revealed the synergistic interaction between Pd and Ag catalyst in the reaction. The unification of these robust catalytic systems ensures optimal outcome in the synthesis of a diverse array of organoselenium compounds featuring aryl-heteroaryl scaffolds.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.