Xiao-Hui Fu , Juan Liao , Zhen-Hua Wang , Zhen-Zhen Ge , Ming-Qiang Zhou , Yong You , Yan-Ping Zhang , Jian-Qiang Zhao , Ji-Hong Lu , Wei-Cheng Yuan
{"title":"钯催化乙烯基恶唑烷-2,4-二酮的脱羧（5 + 5）环化反应：获得十元含 N、O 的杂环","authors":"Xiao-Hui Fu , Juan Liao , Zhen-Hua Wang , Zhen-Zhen Ge , Ming-Qiang Zhou , Yong You , Yan-Ping Zhang , Jian-Qiang Zhao , Ji-Hong Lu , Wei-Cheng Yuan","doi":"10.1039/d4qo00609g","DOIUrl":null,"url":null,"abstract":"<div><div>This study describes a palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones. The cyclization between aza-π-allylpalladium and oxa-π-allylpalladium intermediates, both <em>in situ</em> generated from vinyloxazolidine-2,4-diones, is successfully realized to produce a series of ten-membered N,O-containing heterocycles in up to 90% yield. This work represents a pioneering application of vinyloxazolidine-2,4-diones as oxa-π-allylpalladium species precursors for the construction of heterocyclic compounds.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"11 15","pages":"Pages 4131-4137"},"PeriodicalIF":0.0000,"publicationDate":"2024-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones: access to ten-membered N,O-containing heterocycles†\",\"authors\":\"Xiao-Hui Fu , Juan Liao , Zhen-Hua Wang , Zhen-Zhen Ge , Ming-Qiang Zhou , Yong You , Yan-Ping Zhang , Jian-Qiang Zhao , Ji-Hong Lu , Wei-Cheng Yuan\",\"doi\":\"10.1039/d4qo00609g\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>This study describes a palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones. The cyclization between aza-π-allylpalladium and oxa-π-allylpalladium intermediates, both <em>in situ</em> generated from vinyloxazolidine-2,4-diones, is successfully realized to produce a series of ten-membered N,O-containing heterocycles in up to 90% yield. This work represents a pioneering application of vinyloxazolidine-2,4-diones as oxa-π-allylpalladium species precursors for the construction of heterocyclic compounds.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"11 15\",\"pages\":\"Pages 4131-4137\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-07-23\",\"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/S2052412924004091\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/6/4 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/S2052412924004091","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/6/4 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
A palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones: access to ten-membered N,O-containing heterocycles†
This study describes a palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones. The cyclization between aza-π-allylpalladium and oxa-π-allylpalladium intermediates, both in situ generated from vinyloxazolidine-2,4-diones, is successfully realized to produce a series of ten-membered N,O-containing heterocycles in up to 90% yield. This work represents a pioneering application of vinyloxazolidine-2,4-diones as oxa-π-allylpalladium species precursors for the construction of heterocyclic compounds.
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