{"title":"Palladium/Norbornene Cooperative Catalysis 2-Fold C–H/C–X Coupling: Construction of Polycyclic Aromatic Hydrocarbons from Brominated Benzimidazoles","authors":"Ming-Xuan Wang, Yi-Ming Li, Wei Zeng, Ming-Yao Zhang, Wen-Zhou Yu, Ze-Hui Zheng, Yuan-Yuan Sun, Jin-Heng Li, Yan-Ping Zhu","doi":"10.1021/acs.orglett.5c00298","DOIUrl":null,"url":null,"abstract":"A palladium/norbornene (NBE)-catalyzed 2-fold C–H/C–X coupling reaction of aryl iodides is reported. Bromine-substituted benzimidazoles were chosen as electrophilic and termination reagents, and the versatile polycyclic aromatic hydrocarbon products were successfully obtained. The strategy overcomes the challenge of catalyst poisoning by heterocyclic substrates. In addition, the imidazole moiety in the product is endowed with a localization role, thus enabling the compounds to be applied in a wider synthetic scenario, and the fluorescence persisted. Furthermore, the bioactivity evaluation has identified three promising leading compounds <b>3b</b>, <b>4e</b>, and <b>4i</b>.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"56 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c00298","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A palladium/norbornene (NBE)-catalyzed 2-fold C–H/C–X coupling reaction of aryl iodides is reported. Bromine-substituted benzimidazoles were chosen as electrophilic and termination reagents, and the versatile polycyclic aromatic hydrocarbon products were successfully obtained. The strategy overcomes the challenge of catalyst poisoning by heterocyclic substrates. In addition, the imidazole moiety in the product is endowed with a localization role, thus enabling the compounds to be applied in a wider synthetic scenario, and the fluorescence persisted. Furthermore, the bioactivity evaluation has identified three promising leading compounds 3b, 4e, and 4i.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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