{"title":"Photo-induced synthesis of fluoroalkylated quinolinones via an iron-catalyzed LMCT decarboxylation process†","authors":"Zhuoheng Song, Lin Guo, Chao Yang and Wujiong Xia","doi":"10.1039/D4QO00707G","DOIUrl":null,"url":null,"abstract":"<p >Herein, we report a practical synthetic method for the efficient preparation of fluoroalkylated quinoline-2,4-diones using <em>N</em>-(2-cyanophenyl)-<em>N</em>-methylacrylamides as substrates, fluoroalkyl carboxylic acids as reactants, and Fe(OH)(OAc)<small><sub>2</sub></small> as a catalyst. This reaction started with a photo-driven ligand-to-metal charge transfer (LMCT) process to decarboxylate the reactant and produce fluoroalkyl radicals, which then underwent radical cascade cyclization with the substrate. The target products were obtained in 55–91% yields. A gram scale experiment was also completed using a continuous-flow photocatalytic device.</p>","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://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo00707g","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we report a practical synthetic method for the efficient preparation of fluoroalkylated quinoline-2,4-diones using N-(2-cyanophenyl)-N-methylacrylamides as substrates, fluoroalkyl carboxylic acids as reactants, and Fe(OH)(OAc)2 as a catalyst. This reaction started with a photo-driven ligand-to-metal charge transfer (LMCT) process to decarboxylate the reactant and produce fluoroalkyl radicals, which then underwent radical cascade cyclization with the substrate. The target products were obtained in 55–91% yields. A gram scale experiment was also completed using a 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.