{"title":"Photocatalytic C–H functionalization utilizing acridine−Lewis acid complexes and pyridine N-oxide based HAT catalysts","authors":"Jun Luo, Jujhar Singh, Yongming Deng","doi":"10.1016/j.tet.2025.134683","DOIUrl":null,"url":null,"abstract":"<div><div>Pyridine <em>N</em>-oxides have been well established as a class of potent hydrogen-atom-transfer (HAT) catalysts for C–H functionalization of unactivated alkanes and activated C–H substrates. The combination of acridine derivatives and Lewis acids forms <em>in situ-generated</em> photocatalysts that are able to photo-oxidize pyridine <em>N</em>-oxides to generate <em>N</em>-oxide radicals upon irradiation with visible light. Herein, we described a photocatalytic C–H functionalization utilizing acridine−Lewis acid complexes and pyridine <em>N</em>-oxide based HAT catalysts. The readily available and facilely tunable photocatalytic system of acridine-Lewis acid complexes and pyridine <em>N</em>-oxides enables a broad range of substrates with high reactivities (up to 97 % yield).</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"181 ","pages":"Article 134683"},"PeriodicalIF":2.1000,"publicationDate":"2025-04-26","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/S004040202500239X","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
Pyridine N-oxides have been well established as a class of potent hydrogen-atom-transfer (HAT) catalysts for C–H functionalization of unactivated alkanes and activated C–H substrates. The combination of acridine derivatives and Lewis acids forms in situ-generated photocatalysts that are able to photo-oxidize pyridine N-oxides to generate N-oxide radicals upon irradiation with visible light. Herein, we described a photocatalytic C–H functionalization utilizing acridine−Lewis acid complexes and pyridine N-oxide based HAT catalysts. The readily available and facilely tunable photocatalytic system of acridine-Lewis acid complexes and pyridine N-oxides enables a broad range of substrates with high reactivities (up to 97 % yield).
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.