{"title":"通过铁催化的 LMCT 脱羧过程光诱导合成氟烷基喹啉酮类化合物","authors":"Zhuoheng Song, Lin Guo, Chao Yang, Wujiong Xia","doi":"10.1039/d4qo00707g","DOIUrl":null,"url":null,"abstract":"Herein, we reported an practical synthetic method for the efficient preparation of fluoroalkylated quinoline-2,4-diones using N-(2-cyanophenyl)-N-methylacrylamide as substrates, fluoroalkyl carboxylic acids as reactants, and Fe(OH)(OAc)2 as catalyst. This reaction started from photo-driven ligand-to-metal charge transfer (LMCT) process to decarboxylate and produced fluoroalkyl radicals, which then underwent radical cascade cyclization with the substrate. The target products were obtained in 55-91% yields. Gram scale experiment was also completed by using continuous-flow-photocatalytic-device.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photo-Induced Synthesis of Fluoroalkylated Quinolinones via Iron-Catalyzed LMCT Decarboxylation Process\",\"authors\":\"Zhuoheng Song, Lin Guo, Chao Yang, Wujiong Xia\",\"doi\":\"10.1039/d4qo00707g\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Herein, we reported an practical synthetic method for the efficient preparation of fluoroalkylated quinoline-2,4-diones using N-(2-cyanophenyl)-N-methylacrylamide as substrates, fluoroalkyl carboxylic acids as reactants, and Fe(OH)(OAc)2 as catalyst. This reaction started from photo-driven ligand-to-metal charge transfer (LMCT) process to decarboxylate and produced fluoroalkyl radicals, which then underwent radical cascade cyclization with the substrate. The target products were obtained in 55-91% yields. Gram scale experiment was also completed by using continuous-flow-photocatalytic-device.\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-06-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4qo00707g\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo00707g","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Photo-Induced Synthesis of Fluoroalkylated Quinolinones via Iron-Catalyzed LMCT Decarboxylation Process
Herein, we reported an practical synthetic method for the efficient preparation of fluoroalkylated quinoline-2,4-diones using N-(2-cyanophenyl)-N-methylacrylamide as substrates, fluoroalkyl carboxylic acids as reactants, and Fe(OH)(OAc)2 as catalyst. This reaction started from photo-driven ligand-to-metal charge transfer (LMCT) process to decarboxylate and produced fluoroalkyl radicals, which then underwent radical cascade cyclization with the substrate. The target products were obtained in 55-91% yields. Gram scale experiment was also completed by using continuous-flow-photocatalytic-device.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.