{"title":"Base-Mediated Visible-Light-Driven C–H Arylation of Quinoxalin-2(1H)-Ones in Ethanol","authors":"Yitong Pan, Luohe Wang, Yunhong Shi, Guoqing Huang, Xiubin Bu, Xiaobo Yang, Zhen Zhao","doi":"10.1021/acs.joc.4c01641","DOIUrl":null,"url":null,"abstract":"Prior methods for visible-light-driven C–H arylation of quinoxalin-2(1<i>H</i>)-ones relied on external photocatalysts. Herein, we report a photocatalyst-free approach for this arylation. In this approach, β-dicarbonyl iodonium ylides, combined with <i>t</i>-BuOK in ethanol, act as aryl precursors, forming electron donor–acceptor (EDA) complexes. These complexes enhance light absorption, facilitating efficient single electron transfer and aryl radical formation. Consequently, various quinoxalin-2(1<i>H</i>)-ones undergo precise and efficient arylation without external photocatalysts. This protocol exhibits excellent tolerance toward diverse functional groups, with mild reaction conditions and eco-friendly solvents, revealing a high Ecoscale value.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01641","RegionNum":2,"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
Prior methods for visible-light-driven C–H arylation of quinoxalin-2(1H)-ones relied on external photocatalysts. Herein, we report a photocatalyst-free approach for this arylation. In this approach, β-dicarbonyl iodonium ylides, combined with t-BuOK in ethanol, act as aryl precursors, forming electron donor–acceptor (EDA) complexes. These complexes enhance light absorption, facilitating efficient single electron transfer and aryl radical formation. Consequently, various quinoxalin-2(1H)-ones undergo precise and efficient arylation without external photocatalysts. This protocol exhibits excellent tolerance toward diverse functional groups, with mild reaction conditions and eco-friendly solvents, revealing a high Ecoscale value.
期刊介绍:
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.