Binfeng Zhu , Guokai Li , Mingzhu Li , Deyu Bao , Jingchao Chen , Devendar Ponnam , Baomin Fan
{"title":"可见光介导的n -芳基丙酰胺的无氧化剂串联酰基甲基化/ipso-螺旋环化:获得3-酰基甲基azspiro[4,5]三烯酮","authors":"Binfeng Zhu , Guokai Li , Mingzhu Li , Deyu Bao , Jingchao Chen , Devendar Ponnam , Baomin Fan","doi":"10.1016/j.mcat.2025.115120","DOIUrl":null,"url":null,"abstract":"<div><div>A novel visible-light-mediated acylmethylation/<em>ipso</em>-spirocyclization of <em>N</em>-(<em>p</em>-methoxyaryl)propiolamides with <em>α</em>‑bromo ketones has been developed, enabling the efficient synthesis of diverse 3-acylmethyl functionalized azaspiro[4,5]trienones with high selectivity. This method constructs two new C–C bonds <em>via</em> a sequence of radical C–Br bond cleavage, <em>ipso</em>-spiroanulation and dearomatization. The reaction is operationally simple and scalable and features a broad substrate scope with good functional group tolerance, providing easy access to 3-acylmethyl azaspiro[4,5]trienones.</div></div>","PeriodicalId":393,"journal":{"name":"Molecular Catalysis","volume":"582 ","pages":"Article 115120"},"PeriodicalIF":3.9000,"publicationDate":"2025-05-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible-light-mediated oxidant-free tandem acylmethylation/ipso-spirocyclization of N-arylpropiolamides: Access to 3-acylmethyl azaspiro[4,5]trienones\",\"authors\":\"Binfeng Zhu , Guokai Li , Mingzhu Li , Deyu Bao , Jingchao Chen , Devendar Ponnam , Baomin Fan\",\"doi\":\"10.1016/j.mcat.2025.115120\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A novel visible-light-mediated acylmethylation/<em>ipso</em>-spirocyclization of <em>N</em>-(<em>p</em>-methoxyaryl)propiolamides with <em>α</em>‑bromo ketones has been developed, enabling the efficient synthesis of diverse 3-acylmethyl functionalized azaspiro[4,5]trienones with high selectivity. This method constructs two new C–C bonds <em>via</em> a sequence of radical C–Br bond cleavage, <em>ipso</em>-spiroanulation and dearomatization. The reaction is operationally simple and scalable and features a broad substrate scope with good functional group tolerance, providing easy access to 3-acylmethyl azaspiro[4,5]trienones.</div></div>\",\"PeriodicalId\":393,\"journal\":{\"name\":\"Molecular Catalysis\",\"volume\":\"582 \",\"pages\":\"Article 115120\"},\"PeriodicalIF\":3.9000,\"publicationDate\":\"2025-05-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Molecular Catalysis\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S2468823125003062\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Molecular Catalysis","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2468823125003062","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
Visible-light-mediated oxidant-free tandem acylmethylation/ipso-spirocyclization of N-arylpropiolamides: Access to 3-acylmethyl azaspiro[4,5]trienones
A novel visible-light-mediated acylmethylation/ipso-spirocyclization of N-(p-methoxyaryl)propiolamides with α‑bromo ketones has been developed, enabling the efficient synthesis of diverse 3-acylmethyl functionalized azaspiro[4,5]trienones with high selectivity. This method constructs two new C–C bonds via a sequence of radical C–Br bond cleavage, ipso-spiroanulation and dearomatization. The reaction is operationally simple and scalable and features a broad substrate scope with good functional group tolerance, providing easy access to 3-acylmethyl azaspiro[4,5]trienones.
期刊介绍:
Molecular Catalysis publishes full papers that are original, rigorous, and scholarly contributions examining the molecular and atomic aspects of catalytic activation and reaction mechanisms. The fields covered are:
Heterogeneous catalysis including immobilized molecular catalysts
Homogeneous catalysis including organocatalysis, organometallic catalysis and biocatalysis
Photo- and electrochemistry
Theoretical aspects of catalysis analyzed by computational methods