Yubo Duan , Shu-Ning Lu , Zuguang Yang , Zhengkai Chen , Xiao-Feng Wu
{"title":"Rh(iii)催化的C-H活化/ n -氨基甲酰亚砜酰脲环化反应用于三氟甲基取代(二氢)嘧啶吲哚酮的发散合成","authors":"Yubo Duan , Shu-Ning Lu , Zuguang Yang , Zhengkai Chen , Xiao-Feng Wu","doi":"10.1039/d3qo00803g","DOIUrl":null,"url":null,"abstract":"<div><p>An efficient and straightforward strategy for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones <em>via</em> Rh(<span>iii</span>)-catalyzed C–H activation/annulation of <em>N</em>-carbamoylindoles with CF<sub>3</sub>-imidoyl sulfoxonium ylides has been achieved. The cascade reaction might proceed through a C–H imidoylmethylation, tautomerization and intramolecular nucleophilic addition sequence. A wide range of functionalized pyrimidoindolone derivatives were constructed in good to excellent yields under redox-neutral conditions.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 15","pages":"Pages 3843-3848"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Rh(iii)-catalyzed C–H activation/annulation of N-carbamoylindoles with CF3-imidoyl sulfoxonium ylides for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones†\",\"authors\":\"Yubo Duan , Shu-Ning Lu , Zuguang Yang , Zhengkai Chen , Xiao-Feng Wu\",\"doi\":\"10.1039/d3qo00803g\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>An efficient and straightforward strategy for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones <em>via</em> Rh(<span>iii</span>)-catalyzed C–H activation/annulation of <em>N</em>-carbamoylindoles with CF<sub>3</sub>-imidoyl sulfoxonium ylides has been achieved. The cascade reaction might proceed through a C–H imidoylmethylation, tautomerization and intramolecular nucleophilic addition sequence. A wide range of functionalized pyrimidoindolone derivatives were constructed in good to excellent yields under redox-neutral conditions.</p></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"10 15\",\"pages\":\"Pages 3843-3848\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2023-01-01\",\"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/S2052411023009380\",\"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/S2052411023009380","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Rh(iii)-catalyzed C–H activation/annulation of N-carbamoylindoles with CF3-imidoyl sulfoxonium ylides for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones†
An efficient and straightforward strategy for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones via Rh(iii)-catalyzed C–H activation/annulation of N-carbamoylindoles with CF3-imidoyl sulfoxonium ylides has been achieved. The cascade reaction might proceed through a C–H imidoylmethylation, tautomerization and intramolecular nucleophilic addition sequence. A wide range of functionalized pyrimidoindolone derivatives were constructed in good to excellent yields under redox-neutral conditions.