Yuhao Jiang , Jiapeng Sun , Qi Hu , Jianmin Huang , Yingming Song , Hua Cao , Yue Yu
{"title":"非对映选择性可见光诱导1,6-炔与s -芳基三氟甲烷磺硫酸酯(TTSA)的自由基级联三氟甲基化/硫化/环化","authors":"Yuhao Jiang , Jiapeng Sun , Qi Hu , Jianmin Huang , Yingming Song , Hua Cao , Yue Yu","doi":"10.1039/d4qo01597e","DOIUrl":null,"url":null,"abstract":"<div><div>Under photocatalytic conditions, a novel and highly reactive trifluoromethylating/sulfurating reagent, <em>S</em>-aryl trifluoromethanesulfonothioate (TTSA), was reacted with a variety of 1,6-enynes, affording sulfurated and trifluoromethylated dihydrofuran-2-one or pyrrolidin-2-one derivates in great yields with high diastereoselectivities. In this radical cascade process, three new chemical bonds including C–S, C–C, and C–CF<sub>3</sub> bonds were formed in one step.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 7","pages":"Pages 2242-2247"},"PeriodicalIF":0.0000,"publicationDate":"2025-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Diastereoselective visible-light-induced radical cascade trifluoromethylation/sulfuration/cyclization of 1,6-enynes with S-aryl trifluoromethanesulfonothioate (TTSA)†\",\"authors\":\"Yuhao Jiang , Jiapeng Sun , Qi Hu , Jianmin Huang , Yingming Song , Hua Cao , Yue Yu\",\"doi\":\"10.1039/d4qo01597e\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Under photocatalytic conditions, a novel and highly reactive trifluoromethylating/sulfurating reagent, <em>S</em>-aryl trifluoromethanesulfonothioate (TTSA), was reacted with a variety of 1,6-enynes, affording sulfurated and trifluoromethylated dihydrofuran-2-one or pyrrolidin-2-one derivates in great yields with high diastereoselectivities. In this radical cascade process, three new chemical bonds including C–S, C–C, and C–CF<sub>3</sub> bonds were formed in one step.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 7\",\"pages\":\"Pages 2242-2247\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-02-12\",\"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/S2052412925000609\",\"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/S2052412925000609","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Diastereoselective visible-light-induced radical cascade trifluoromethylation/sulfuration/cyclization of 1,6-enynes with S-aryl trifluoromethanesulfonothioate (TTSA)†
Under photocatalytic conditions, a novel and highly reactive trifluoromethylating/sulfurating reagent, S-aryl trifluoromethanesulfonothioate (TTSA), was reacted with a variety of 1,6-enynes, affording sulfurated and trifluoromethylated dihydrofuran-2-one or pyrrolidin-2-one derivates in great yields with high diastereoselectivities. In this radical cascade process, three new chemical bonds including C–S, C–C, and C–CF3 bonds were formed in one step.