{"title":"可见光促进咪唑类支架结构的脱芳化","authors":"Silvia Roscales, Aurelio G. Csáky","doi":"10.1002/adsc.70084","DOIUrl":null,"url":null,"abstract":"Dearomatization is a powerful strategy for constructing complex carbocycles and heterocycles, though it typically relies on harsh conditions due to aromatic stability. Herein, a visible‐light‐driven photocatalytic dearomatization strategy for electron‐poor imidazo[1,2‐<jats:italic>a</jats:italic>]pyridines is reported, addressing a key limitation of current methods, which predominantly target electron‐rich aromatic systems. Using <jats:italic>α</jats:italic>‐keto acids as acyl radical precursors, this mild method enables the efficient synthesis of structurally diverse and functionalized imidazole derivatives, a privileged scaffold in pharmaceuticals and advanced materials. Some of the synthesized imidazoles display noteworthy photophysical properties. Some of the synthesized imidazoles show dual fluorescence from deep violet to greenish‐cyan, highlighting potential as innovative fluorescent probes. This work expands the scope of dearomatization and provides a valuable tool for accessing new chemical space in drug discovery and materials science.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"29 1","pages":""},"PeriodicalIF":4.0000,"publicationDate":"2025-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible‐Light‐Promoted Dearomatization for The Construction of Imidazole Scaffolds\",\"authors\":\"Silvia Roscales, Aurelio G. Csáky\",\"doi\":\"10.1002/adsc.70084\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Dearomatization is a powerful strategy for constructing complex carbocycles and heterocycles, though it typically relies on harsh conditions due to aromatic stability. Herein, a visible‐light‐driven photocatalytic dearomatization strategy for electron‐poor imidazo[1,2‐<jats:italic>a</jats:italic>]pyridines is reported, addressing a key limitation of current methods, which predominantly target electron‐rich aromatic systems. Using <jats:italic>α</jats:italic>‐keto acids as acyl radical precursors, this mild method enables the efficient synthesis of structurally diverse and functionalized imidazole derivatives, a privileged scaffold in pharmaceuticals and advanced materials. Some of the synthesized imidazoles display noteworthy photophysical properties. Some of the synthesized imidazoles show dual fluorescence from deep violet to greenish‐cyan, highlighting potential as innovative fluorescent probes. This work expands the scope of dearomatization and provides a valuable tool for accessing new chemical space in drug discovery and materials science.\",\"PeriodicalId\":118,\"journal\":{\"name\":\"Advanced Synthesis & Catalysis\",\"volume\":\"29 1\",\"pages\":\"\"},\"PeriodicalIF\":4.0000,\"publicationDate\":\"2025-08-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Advanced Synthesis & Catalysis\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1002/adsc.70084\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.70084","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
Visible‐Light‐Promoted Dearomatization for The Construction of Imidazole Scaffolds
Dearomatization is a powerful strategy for constructing complex carbocycles and heterocycles, though it typically relies on harsh conditions due to aromatic stability. Herein, a visible‐light‐driven photocatalytic dearomatization strategy for electron‐poor imidazo[1,2‐a]pyridines is reported, addressing a key limitation of current methods, which predominantly target electron‐rich aromatic systems. Using α‐keto acids as acyl radical precursors, this mild method enables the efficient synthesis of structurally diverse and functionalized imidazole derivatives, a privileged scaffold in pharmaceuticals and advanced materials. Some of the synthesized imidazoles display noteworthy photophysical properties. Some of the synthesized imidazoles show dual fluorescence from deep violet to greenish‐cyan, highlighting potential as innovative fluorescent probes. This work expands the scope of dearomatization and provides a valuable tool for accessing new chemical space in drug discovery and materials science.
期刊介绍:
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.