{"title":"利用n -氟苯磺酰亚胺(NFSI)作为双功能多米诺试剂的远程激活策略激活(RASE) π键迁移脱烷基C-N偶联","authors":"Jiahao Gu, Zhenyang Wan, Yuhong Lu, Xiangmin Tian, Ziyue Zeng, Dailin Zhuang, Ziyuan Li","doi":"10.1039/d5qo00480b","DOIUrl":null,"url":null,"abstract":"Remote activating strategy enabled (RASE) π-bond migratory dealkylative C(sp3)-N and C(sp2)-N coupling with 2-alkoxylthiazole through C(sp3)-H and C(sp2)-H cleavage, giving N-benzyl or N-phenyl thiazol-2(3H)-one, respectively, are achieved under mild conditions. N-Fluorobenzenesulfonimide (NFSI) serves as a crucial bifunctional domino reagent which not only generates nitrogen-centred radical that initiates N-C or N-N radical relay, offering electrophile coupling partner, but also provides the key carbocation scavenger, N-hydrobenzenesulfonimide (NHSI), triggering π-bond migratory dealkylation of 2-alkoxylthiazole which offers nucleophilic thiazol-2(3H)-one coupling partner. Plausible mechanism has been proposed based on the results of mechanistic studies.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"37 1","pages":""},"PeriodicalIF":4.7000,"publicationDate":"2025-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Remote Activating Strategy Enabled (RASE) π-Bond Migratory Dealkylative C-N coupling Utilising N-Fluorobenzenesulfonimide (NFSI) as A Bifunctional Domino Reagent\",\"authors\":\"Jiahao Gu, Zhenyang Wan, Yuhong Lu, Xiangmin Tian, Ziyue Zeng, Dailin Zhuang, Ziyuan Li\",\"doi\":\"10.1039/d5qo00480b\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Remote activating strategy enabled (RASE) π-bond migratory dealkylative C(sp3)-N and C(sp2)-N coupling with 2-alkoxylthiazole through C(sp3)-H and C(sp2)-H cleavage, giving N-benzyl or N-phenyl thiazol-2(3H)-one, respectively, are achieved under mild conditions. N-Fluorobenzenesulfonimide (NFSI) serves as a crucial bifunctional domino reagent which not only generates nitrogen-centred radical that initiates N-C or N-N radical relay, offering electrophile coupling partner, but also provides the key carbocation scavenger, N-hydrobenzenesulfonimide (NHSI), triggering π-bond migratory dealkylation of 2-alkoxylthiazole which offers nucleophilic thiazol-2(3H)-one coupling partner. Plausible mechanism has been proposed based on the results of mechanistic studies.\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":\"37 1\",\"pages\":\"\"},\"PeriodicalIF\":4.7000,\"publicationDate\":\"2025-06-03\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d5qo00480b\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5qo00480b","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Remote Activating Strategy Enabled (RASE) π-Bond Migratory Dealkylative C-N coupling Utilising N-Fluorobenzenesulfonimide (NFSI) as A Bifunctional Domino Reagent
Remote activating strategy enabled (RASE) π-bond migratory dealkylative C(sp3)-N and C(sp2)-N coupling with 2-alkoxylthiazole through C(sp3)-H and C(sp2)-H cleavage, giving N-benzyl or N-phenyl thiazol-2(3H)-one, respectively, are achieved under mild conditions. N-Fluorobenzenesulfonimide (NFSI) serves as a crucial bifunctional domino reagent which not only generates nitrogen-centred radical that initiates N-C or N-N radical relay, offering electrophile coupling partner, but also provides the key carbocation scavenger, N-hydrobenzenesulfonimide (NHSI), triggering π-bond migratory dealkylation of 2-alkoxylthiazole which offers nucleophilic thiazol-2(3H)-one coupling partner. Plausible mechanism has been proposed based on the results of mechanistic studies.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.