{"title":"定向亲核芳香取代反应。","authors":"Yasuyuki Nitta , Yusei Nakashima , Michinori Sumimoto , Takashi Nishikata","doi":"10.1039/d4cc04912h","DOIUrl":null,"url":null,"abstract":"<div><div>In this study, we discovered a directed nucleophilic aromatic substitution reaction, “directed SNAr (dSNAr),” in the reaction of <em>ortho</em>-iodobezamides and amine in the presence of pyridine. The reaction proceeded <em>ortho</em>-specifically and did not require a strong electron-withdrawing group on the arene substrate. Most reactions proceeded at room temperature in the presence of Py, and a wide range of amine nucleophiles can be applied. Furthermore, the reactions with benzamide substituted with multiple halogens were found to be 100% <em>ortho</em>-selective.</div></div>","PeriodicalId":67,"journal":{"name":"Chemical Communications","volume":"60 96","pages":"Pages 14284-14287"},"PeriodicalIF":4.2000,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Directed nucleophilic aromatic substitution reaction†\",\"authors\":\"Yasuyuki Nitta , Yusei Nakashima , Michinori Sumimoto , Takashi Nishikata\",\"doi\":\"10.1039/d4cc04912h\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>In this study, we discovered a directed nucleophilic aromatic substitution reaction, “directed SNAr (dSNAr),” in the reaction of <em>ortho</em>-iodobezamides and amine in the presence of pyridine. The reaction proceeded <em>ortho</em>-specifically and did not require a strong electron-withdrawing group on the arene substrate. Most reactions proceeded at room temperature in the presence of Py, and a wide range of amine nucleophiles can be applied. Furthermore, the reactions with benzamide substituted with multiple halogens were found to be 100% <em>ortho</em>-selective.</div></div>\",\"PeriodicalId\":67,\"journal\":{\"name\":\"Chemical Communications\",\"volume\":\"60 96\",\"pages\":\"Pages 14284-14287\"},\"PeriodicalIF\":4.2000,\"publicationDate\":\"2024-11-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemical Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1359734524023589\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1359734524023589","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
In this study, we discovered a directed nucleophilic aromatic substitution reaction, “directed SNAr (dSNAr),” in the reaction of ortho-iodobezamides and amine in the presence of pyridine. The reaction proceeded ortho-specifically and did not require a strong electron-withdrawing group on the arene substrate. Most reactions proceeded at room temperature in the presence of Py, and a wide range of amine nucleophiles can be applied. Furthermore, the reactions with benzamide substituted with multiple halogens were found to be 100% ortho-selective.
期刊介绍:
ChemComm (Chemical Communications) is renowned as the fastest publisher of articles providing information on new avenues of research, drawn from all the world''s major areas of chemical research.