Mengxin Li , Molai Zhao , Xianglin Zhong , Xiaoqing Wen , Xiangwei Liu , Hezhong Jiang , Rui Tan , Jiahong Li
{"title":"可见光介导的硝基烯烃和烯烃的 [1+2+2] 环加成反应","authors":"Mengxin Li , Molai Zhao , Xianglin Zhong , Xiaoqing Wen , Xiangwei Liu , Hezhong Jiang , Rui Tan , Jiahong Li","doi":"10.1039/d4qo01418a","DOIUrl":null,"url":null,"abstract":"<div><div>We report a visible light-mediated [1 + 2 + 2] cycloaddition reaction between nitroarenes and alkenes, conducted under mild conditions, to synthesize isoxazolidines. This method operates without photocatalysts or transition metal catalysts. Mechanistic studies suggest that under light irradiation, the alkene interacts with the triplet state nitroarene to form a nitrone intermediate, acting as a C1 source. This intermediate undergoes a [3 + 2] cycloaddition with the alkene, resulting in the desired product.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 2","pages":"Pages 636-640"},"PeriodicalIF":0.0000,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible light-mediated [1 + 2 + 2] cycloaddition reaction of nitroarenes and alkenes†\",\"authors\":\"Mengxin Li , Molai Zhao , Xianglin Zhong , Xiaoqing Wen , Xiangwei Liu , Hezhong Jiang , Rui Tan , Jiahong Li\",\"doi\":\"10.1039/d4qo01418a\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>We report a visible light-mediated [1 + 2 + 2] cycloaddition reaction between nitroarenes and alkenes, conducted under mild conditions, to synthesize isoxazolidines. This method operates without photocatalysts or transition metal catalysts. Mechanistic studies suggest that under light irradiation, the alkene interacts with the triplet state nitroarene to form a nitrone intermediate, acting as a C1 source. This intermediate undergoes a [3 + 2] cycloaddition with the alkene, resulting in the desired product.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 2\",\"pages\":\"Pages 636-640\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-11-19\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S2052412924008106\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/11/14 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412924008106","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/11/14 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
Visible light-mediated [1 + 2 + 2] cycloaddition reaction of nitroarenes and alkenes†
We report a visible light-mediated [1 + 2 + 2] cycloaddition reaction between nitroarenes and alkenes, conducted under mild conditions, to synthesize isoxazolidines. This method operates without photocatalysts or transition metal catalysts. Mechanistic studies suggest that under light irradiation, the alkene interacts with the triplet state nitroarene to form a nitrone intermediate, acting as a C1 source. This intermediate undergoes a [3 + 2] cycloaddition with the alkene, resulting in the desired product.