{"title":"Sustainable Synthesis of 3-Acylmethylated Coumarins via Photoredox Catalytic Radical Addition/Cyclization in Aqueous Media.","authors":"Binfeng Zhu, Devendar Ponnam, Mingzhu Li, Guokai Li, Ruifeng Fan, Jingchao Chen, Baomin Fan","doi":"10.1021/acs.joc.5c00608","DOIUrl":null,"url":null,"abstract":"<p><p>A photoredox catalytic cascade radical reaction for the addition/cyclization of arylalkynoates with α-bromoketones in water at room temperature has been developed, offering a green and efficient approach for synthesizing 3-acylmethylated coumarins. This method eliminates the need for conventional organic solvents, phase-transfer catalysts, and excess oxidants, ensuring operational simplicity and environmental sustainability. The reaction is scalable, accommodates a broad array of substrates with outstanding tolerance for functional groups, and offers a versatile route to biologically valuable coumarins.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.5c00608","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
A photoredox catalytic cascade radical reaction for the addition/cyclization of arylalkynoates with α-bromoketones in water at room temperature has been developed, offering a green and efficient approach for synthesizing 3-acylmethylated coumarins. This method eliminates the need for conventional organic solvents, phase-transfer catalysts, and excess oxidants, ensuring operational simplicity and environmental sustainability. The reaction is scalable, accommodates a broad array of substrates with outstanding tolerance for functional groups, and offers a versatile route to biologically valuable coumarins.
期刊介绍:
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.