{"title":"Programmable Synthesis of Cationic Azaperylenes via Rh(III)-Catalyzed Multiple C–H/N–H Bonds Activation and Annulation","authors":"Hui Li, Yiling Zeng, Fangpeng Liang, Yanyan Yang, Kaida Li, Futao Pang, Shiqing Li","doi":"10.1021/acs.orglett.4c04269","DOIUrl":null,"url":null,"abstract":"Rh(III)-catalyzed dual N–H and triple C–H activation/(4 + 2) annulation of 2-aryl-2,3-dihydro-1<i>H</i>-perimidines and alkynes has been disclosed to construct 4,5,14,15-tetrasubstituted cationic azaperylenes with high yields (up to 95%) and broad scope. Tandem (4 + 2) annulation of 1<i>H</i>-perimidines with vinylene carbonate and alkynes affords 4,5-disubstituted azaperylene salts, and <i>ortho</i>-alkynyl 1<i>H</i>-perimidines undergo an intra- and intermolecular annulation cascade to give 4,5,14-trisubstituted targets. Most of the intermediates were detected by ESI-MS, indicating a convincible mechanism including three possible paths. The resultant new cationic azaperylenes generally exhibit yellow to red emissions (540–642 nm), and the disubstituted cations exhibit longer emission wavelengths than their tri- and tetra-substituted partners. This protocol also offers a concise and efficient tool to construct perimidinium-based dications, showing potential applications in electrochromic devices.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"23 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-17","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.4c04269","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
Rh(III)-catalyzed dual N–H and triple C–H activation/(4 + 2) annulation of 2-aryl-2,3-dihydro-1H-perimidines and alkynes has been disclosed to construct 4,5,14,15-tetrasubstituted cationic azaperylenes with high yields (up to 95%) and broad scope. Tandem (4 + 2) annulation of 1H-perimidines with vinylene carbonate and alkynes affords 4,5-disubstituted azaperylene salts, and ortho-alkynyl 1H-perimidines undergo an intra- and intermolecular annulation cascade to give 4,5,14-trisubstituted targets. Most of the intermediates were detected by ESI-MS, indicating a convincible mechanism including three possible paths. The resultant new cationic azaperylenes generally exhibit yellow to red emissions (540–642 nm), and the disubstituted cations exhibit longer emission wavelengths than their tri- and tetra-substituted partners. This protocol also offers a concise and efficient tool to construct perimidinium-based dications, showing potential applications in electrochromic devices.
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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