Molai Zhao , Yutong Liu , Xueqin Chen , Min Peng , Yawen Wang , Xiangwei Liu , Hezhong Jiang , Rui Tan , Jiahong Li
{"title":"Photocatalyst-free formate-mediated C–O cleavage by the EDA complex and SCS strategy for the synthesis of diaryl 1,4-diketone in air†","authors":"Molai Zhao , Yutong Liu , Xueqin Chen , Min Peng , Yawen Wang , Xiangwei Liu , Hezhong Jiang , Rui Tan , Jiahong Li","doi":"10.1039/d4ob01913j","DOIUrl":null,"url":null,"abstract":"<div><div>Under mild visible light conditions, formates facilitate C–O cleavage <em>via</em> the EDA complex and SCS strategy, yielding α-carbonyl alkyl radicals. These radicals then react with olefins under air conditions, leading to the synthesis of diaryl 1,4-dicarbonyl compounds. Mechanistic studies reveal that α-formyloxy ketone is generated <em>in situ</em> by the reaction between α-brominated acetophenone and formates, followed by the formation of the EDA complex. Additionally, formates also serve as a single-electron reducing reagent in the reaction.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 9","pages":"Pages 2079-2085"},"PeriodicalIF":2.7000,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052025000400","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/10 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Under mild visible light conditions, formates facilitate C–O cleavage via the EDA complex and SCS strategy, yielding α-carbonyl alkyl radicals. These radicals then react with olefins under air conditions, leading to the synthesis of diaryl 1,4-dicarbonyl compounds. Mechanistic studies reveal that α-formyloxy ketone is generated in situ by the reaction between α-brominated acetophenone and formates, followed by the formation of the EDA complex. Additionally, formates also serve as a single-electron reducing reagent in the reaction.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.