Jia-Huan Cui , Mei Tan , Jun Zhang , Yan He , Xingguang Li , Pei-Nian Liu
{"title":"高选择性可见光诱导叠氮基亚砜酰乙烯级联环化:合成三取代呋喃的新方法","authors":"Jia-Huan Cui , Mei Tan , Jun Zhang , Yan He , Xingguang Li , Pei-Nian Liu","doi":"10.1039/d4qo02195a","DOIUrl":null,"url":null,"abstract":"<div><div>A simple protocol for the synthesis of trisubstituted furans <em>via</em> visible-light-driven regioselective cascade cyclization of vinyl sulfoxonium ylides with azides has been achieved. The reaction proceeds through the formation of a novel α-enone-α′-amide sulfoxonium ylide, which undergoes cyclization upon blue light irradiation to yield a trisubstituted furan scaffold. This method offers advantages including the absence of transition metals and photocatalysts, and the desired trisubstituted furans were prepared in good to excellent yields.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 1905-1910"},"PeriodicalIF":0.0000,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Highly selective visible-light-induced cascade cyclization of vinyl sulfoxonium ylides with azides: a novel synthetic approach towards trisubstituted furans†\",\"authors\":\"Jia-Huan Cui , Mei Tan , Jun Zhang , Yan He , Xingguang Li , Pei-Nian Liu\",\"doi\":\"10.1039/d4qo02195a\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A simple protocol for the synthesis of trisubstituted furans <em>via</em> visible-light-driven regioselective cascade cyclization of vinyl sulfoxonium ylides with azides has been achieved. The reaction proceeds through the formation of a novel α-enone-α′-amide sulfoxonium ylide, which undergoes cyclization upon blue light irradiation to yield a trisubstituted furan scaffold. This method offers advantages including the absence of transition metals and photocatalysts, and the desired trisubstituted furans were prepared in good to excellent yields.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 6\",\"pages\":\"Pages 1905-1910\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-01-22\",\"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/S2052412925000439\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/1/14 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/S2052412925000439","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/14 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
Highly selective visible-light-induced cascade cyclization of vinyl sulfoxonium ylides with azides: a novel synthetic approach towards trisubstituted furans†
A simple protocol for the synthesis of trisubstituted furans via visible-light-driven regioselective cascade cyclization of vinyl sulfoxonium ylides with azides has been achieved. The reaction proceeds through the formation of a novel α-enone-α′-amide sulfoxonium ylide, which undergoes cyclization upon blue light irradiation to yield a trisubstituted furan scaffold. This method offers advantages including the absence of transition metals and photocatalysts, and the desired trisubstituted furans were prepared in good to excellent yields.