Mengyue Dai, Mengqin Liu, Xin Wang, Tao Qin*, Heye Zhou and Bin Liu*,
{"title":"Thioesterification of Polyfluoroarenes via Copper-Catalyzed Radical Cross-Coupling with K2S and Aldehydes in Water","authors":"Mengyue Dai, Mengqin Liu, Xin Wang, Tao Qin*, Heye Zhou and Bin Liu*, ","doi":"10.1021/acs.orglett.5c03572","DOIUrl":null,"url":null,"abstract":"<p >A novel copper-catalyzed radical cross-coupling reaction for the thioesterification of polyfluoroarenes is developed using K<sub>2</sub>S and aldehydes in water. This protocol employs a readily available K<sub>2</sub>S as a sulfur source, eliminating the need for hazardous thiols and organic solvents. The mild reaction conditions are compatible with a wide range of functional groups, providing access to diverse polyfluoroaryl thioesters. The mechanistic study not only demonstrates the significant role of K<sub>2</sub>S in activating polyfluoroarenes but also proposes that the reaction involves nitrogen radicals abstracting α-hydrogens from aldehydes to yield acyl radicals, which participate in a cross-coupling process with thiyl radicals. The applicability of this thioester in synthetic transformations demonstrates its enhanced reactivity as an acylating agent.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 37","pages":"10607–10613"},"PeriodicalIF":5.0000,"publicationDate":"2025-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03572","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
A novel copper-catalyzed radical cross-coupling reaction for the thioesterification of polyfluoroarenes is developed using K2S and aldehydes in water. This protocol employs a readily available K2S as a sulfur source, eliminating the need for hazardous thiols and organic solvents. The mild reaction conditions are compatible with a wide range of functional groups, providing access to diverse polyfluoroaryl thioesters. The mechanistic study not only demonstrates the significant role of K2S in activating polyfluoroarenes but also proposes that the reaction involves nitrogen radicals abstracting α-hydrogens from aldehydes to yield acyl radicals, which participate in a cross-coupling process with thiyl radicals. The applicability of this thioester in synthetic transformations demonstrates its enhanced reactivity as an acylating agent.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
