{"title":"[双(三氟乙酰氧基)碘]苯介导的α-氧酮二硫缩醛的区域选择性(sp2) -H硒化反应","authors":"Anirban Mandal, Sanjay Roy, Sajal Das","doi":"10.1016/j.tetlet.2025.155685","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, we report a regioselective C(sp<sup>2</sup>)–H bond selenylation of α-oxo ketene dithioacetals mediated by [Bis(trifluoroacetoxy)iodo]-benzene (PIFA) using readily available organodiselenides. A library of structurally diverse selenoether derivatives is prepared with a high yield of 92 %. This reaction occurs at ambient temperature and does not require any transition metal catalyst. An in-depth study has also been done to enlighten the reaction pathway. The reaction is found to be equally active in up-scale synthesis.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155685"},"PeriodicalIF":1.5000,"publicationDate":"2025-06-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"[Bis(trifluoroacetoxy)iodo]benzene mediated regioselectivec(sp2)–H selenylation of α-oxo ketene dithioacetals under ambient conditions\",\"authors\":\"Anirban Mandal, Sanjay Roy, Sajal Das\",\"doi\":\"10.1016/j.tetlet.2025.155685\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Herein, we report a regioselective C(sp<sup>2</sup>)–H bond selenylation of α-oxo ketene dithioacetals mediated by [Bis(trifluoroacetoxy)iodo]-benzene (PIFA) using readily available organodiselenides. A library of structurally diverse selenoether derivatives is prepared with a high yield of 92 %. This reaction occurs at ambient temperature and does not require any transition metal catalyst. An in-depth study has also been done to enlighten the reaction pathway. The reaction is found to be equally active in up-scale synthesis.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":\"168 \",\"pages\":\"Article 155685\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2025-06-06\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403925002345\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403925002345","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
[Bis(trifluoroacetoxy)iodo]benzene mediated regioselectivec(sp2)–H selenylation of α-oxo ketene dithioacetals under ambient conditions
Herein, we report a regioselective C(sp2)–H bond selenylation of α-oxo ketene dithioacetals mediated by [Bis(trifluoroacetoxy)iodo]-benzene (PIFA) using readily available organodiselenides. A library of structurally diverse selenoether derivatives is prepared with a high yield of 92 %. This reaction occurs at ambient temperature and does not require any transition metal catalyst. An in-depth study has also been done to enlighten the reaction pathway. The reaction is found to be equally active in up-scale synthesis.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.