芳基烷基醚的光催化脱烷基反应

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-05 DOI:10.1021/acs.orglett.5c01831

Yi Li, Mengjie Song, Sha Luo, Chunhui Ma, Wei Li, Shujun Li, Zhijun Chen, Shouxin Liu, Honglei Chen, Bing Tian

{"title":"芳基烷基醚的光催化脱烷基反应","authors":"Yi Li, Mengjie Song, Sha Luo, Chunhui Ma, Wei Li, Shujun Li, Zhijun Chen, Shouxin Liu, Honglei Chen, Bing Tian","doi":"10.1021/acs.orglett.5c01831","DOIUrl":null,"url":null,"abstract":"A copper-photocatalyzed dealkylation of aryl alkyl ethers is established by using O<sub>2</sub> as an oxidant. This methodology demonstrates exceptional practicality through mild reaction conditions, an economical and stable catalytic system, operational simplicity, high conversion efficiency, scalability to 10 g, and broad substrate generality. Mechanistic investigations reveal that the chlorine radical mediates substrate activation, followed by oxidation and hydrolysis to achieve dealkylation. This mild and efficient method can be a competitive alternative for aryl ether deprotection.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"7 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photocatalytic Dealkylation of Aryl Alkyl Ethers\",\"authors\":\"Yi Li, Mengjie Song, Sha Luo, Chunhui Ma, Wei Li, Shujun Li, Zhijun Chen, Shouxin Liu, Honglei Chen, Bing Tian\",\"doi\":\"10.1021/acs.orglett.5c01831\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A copper-photocatalyzed dealkylation of aryl alkyl ethers is established by using O<sub>2</sub> as an oxidant. This methodology demonstrates exceptional practicality through mild reaction conditions, an economical and stable catalytic system, operational simplicity, high conversion efficiency, scalability to 10 g, and broad substrate generality. Mechanistic investigations reveal that the chlorine radical mediates substrate activation, followed by oxidation and hydrolysis to achieve dealkylation. This mild and efficient method can be a competitive alternative for aryl ether deprotection.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"7 1\",\"pages\":\"\"},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2025-06-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.5c01831\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c01831","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

摘要

以氧为氧化剂，建立了铜光催化芳基烷基醚脱烷基反应。该方法通过温和的反应条件、经济稳定的催化系统、操作简单、高转化效率、可扩展到10g和广泛的底物通用性证明了卓越的实用性。机理研究表明，氯自由基介导底物活化，随后氧化和水解，以实现脱烷基。这种温和而有效的方法可以成为芳基醚脱保护的有竞争力的替代方法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Photocatalytic Dealkylation of Aryl Alkyl Ethers

查看原文本刊更多论文

Photocatalytic Dealkylation of Aryl Alkyl Ethers

A copper-photocatalyzed dealkylation of aryl alkyl ethers is established by using O₂ as an oxidant. This methodology demonstrates exceptional practicality through mild reaction conditions, an economical and stable catalytic system, operational simplicity, high conversion efficiency, scalability to 10 g, and broad substrate generality. Mechanistic investigations reveal that the chlorine radical mediates substrate activation, followed by oxidation and hydrolysis to achieve dealkylation. This mild and efficient method can be a competitive alternative for aryl ether deprotection.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

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.