Zi-Hang Yuan , Hong Xin , Yuan Gao , Guo-Wei Sun , Rui-Ying Zhao , Xin-Hua Duan , Li-Na Guo
{"title":"光氧化催化的 α、α-二氟芳基乙酸酯和酰胺的选择性脱氚脱氟反应","authors":"Zi-Hang Yuan , Hong Xin , Yuan Gao , Guo-Wei Sun , Rui-Ying Zhao , Xin-Hua Duan , Li-Na Guo","doi":"10.1039/d4qo00781f","DOIUrl":null,"url":null,"abstract":"<div><div>A highly selective photocatalytic deuterodefluorination of fluorinated esters with D<sub>2</sub>O is presented. By tailoring the catalytic system, a variety of α,α-difluoroaryl acetates underwent selective defluorination/deuteration to afford the 2-fluoro-2-arylacetate-<em>d</em> and 2-arylacetate-<em>d</em><sub>2</sub> in good yields with excellent deuteration rate. Satisfactorily, this protocol was successfully applied to deuterate some drug molecules, such as the felbinacethyl-<em>d</em><sub>2</sub> and felbilnac-<em>d</em><sub>2</sub>.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"11 16","pages":"Pages 4479-4486"},"PeriodicalIF":0.0000,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photoredox-catalyzed selective deuterodefluorination of α,α-difluoroarylacetic esters and amides†\",\"authors\":\"Zi-Hang Yuan , Hong Xin , Yuan Gao , Guo-Wei Sun , Rui-Ying Zhao , Xin-Hua Duan , Li-Na Guo\",\"doi\":\"10.1039/d4qo00781f\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A highly selective photocatalytic deuterodefluorination of fluorinated esters with D<sub>2</sub>O is presented. By tailoring the catalytic system, a variety of α,α-difluoroaryl acetates underwent selective defluorination/deuteration to afford the 2-fluoro-2-arylacetate-<em>d</em> and 2-arylacetate-<em>d</em><sub>2</sub> in good yields with excellent deuteration rate. Satisfactorily, this protocol was successfully applied to deuterate some drug molecules, such as the felbinacethyl-<em>d</em><sub>2</sub> and felbilnac-<em>d</em><sub>2</sub>.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"11 16\",\"pages\":\"Pages 4479-4486\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-06-18\",\"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/S2052412924004601\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/6/22 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/S2052412924004601","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/6/22 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
Photoredox-catalyzed selective deuterodefluorination of α,α-difluoroarylacetic esters and amides†
A highly selective photocatalytic deuterodefluorination of fluorinated esters with D2O is presented. By tailoring the catalytic system, a variety of α,α-difluoroaryl acetates underwent selective defluorination/deuteration to afford the 2-fluoro-2-arylacetate-d and 2-arylacetate-d2 in good yields with excellent deuteration rate. Satisfactorily, this protocol was successfully applied to deuterate some drug molecules, such as the felbinacethyl-d2 and felbilnac-d2.
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