Yuan-Yi Lu , Guirong You , Yu Teng , Jun Zhao , Yi-Dong Zhong , Hong-Shuang Li
{"title":"铑催化乙烯基苯并噁嗪酮的区域选择性脱羧氢硒化和氢硫化反应","authors":"Yuan-Yi Lu , Guirong You , Yu Teng , Jun Zhao , Yi-Dong Zhong , Hong-Shuang Li","doi":"10.1039/d4qo02084g","DOIUrl":null,"url":null,"abstract":"<div><div>A rhodium(<span>i</span>)-catalyzed decarboxylative hydrochalcogenation of diverse vinyl benzoxazinanones is developed. The coupling of selenols or their surrogates with substrates provides allylic selenides with excellent linear- and <em>E</em>-selectivity, while the transformation of thiols delivers allylic sulfides with remarkable branch-selectivity. The broad substrate scope in combination with satisfactory functional group tolerance makes this protocol a new paradigm for regioselective hydrofunctionalization that involves reactive π-allylmetal species.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 12","pages":"Pages 3606-3613"},"PeriodicalIF":0.0000,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Rhodium-catalyzed regioselective decarboxylative hydroselenation and hydrothiolation of vinyl benzoxazinanones†\",\"authors\":\"Yuan-Yi Lu , Guirong You , Yu Teng , Jun Zhao , Yi-Dong Zhong , Hong-Shuang Li\",\"doi\":\"10.1039/d4qo02084g\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A rhodium(<span>i</span>)-catalyzed decarboxylative hydrochalcogenation of diverse vinyl benzoxazinanones is developed. The coupling of selenols or their surrogates with substrates provides allylic selenides with excellent linear- and <em>E</em>-selectivity, while the transformation of thiols delivers allylic sulfides with remarkable branch-selectivity. The broad substrate scope in combination with satisfactory functional group tolerance makes this protocol a new paradigm for regioselective hydrofunctionalization that involves reactive π-allylmetal species.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 12\",\"pages\":\"Pages 3606-3613\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-03-03\",\"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/S2052412925001901\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"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/S2052412925001901","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Rhodium-catalyzed regioselective decarboxylative hydroselenation and hydrothiolation of vinyl benzoxazinanones†
A rhodium(i)-catalyzed decarboxylative hydrochalcogenation of diverse vinyl benzoxazinanones is developed. The coupling of selenols or their surrogates with substrates provides allylic selenides with excellent linear- and E-selectivity, while the transformation of thiols delivers allylic sulfides with remarkable branch-selectivity. The broad substrate scope in combination with satisfactory functional group tolerance makes this protocol a new paradigm for regioselective hydrofunctionalization that involves reactive π-allylmetal species.