以邻烷基烯醇为前驱体的可见光诱导邻醌原位合成串联[4 + 2]环加成反应

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-26 DOI:10.1021/acs.orglett.4c04494

Shu Wang, Ge Liang, Cheng Wang, Chen-Hong Wang, Zhiyuan Huang, Chen-Ho Tung, Li-Zhu Wu

{"title":"以邻烷基烯醇为前驱体的可见光诱导邻醌原位合成串联[4 + 2]环加成反应","authors":"Shu Wang, Ge Liang, Cheng Wang, Chen-Hong Wang, Zhiyuan Huang, Chen-Ho Tung, Li-Zhu Wu","doi":"10.1021/acs.orglett.4c04494","DOIUrl":null,"url":null,"abstract":"Reported herein is the generation of ortho-quinone methides (o-QMs) via metal-free visible-light-induced oxidation of ortho-alkylarenols, as well as their subsequent reaction with olefins to afford chromans in good to excellent yields (up to 91%). The key is the selective activation of the benzylic C(sp3)–H bond of ortho-alkylarenols via single electron transfer (SET) and the formation of o-QMs via hydrogen atom transfer (HAT).","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"1 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2024-12-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction\",\"authors\":\"Shu Wang, Ge Liang, Cheng Wang, Chen-Hong Wang, Zhiyuan Huang, Chen-Ho Tung, Li-Zhu Wu\",\"doi\":\"10.1021/acs.orglett.4c04494\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Reported herein is the generation of ortho-quinone methides (o-QMs) via metal-free visible-light-induced oxidation of ortho-alkylarenols, as well as their subsequent reaction with olefins to afford chromans in good to excellent yields (up to 91%). The key is the selective activation of the benzylic C(sp3)–H bond of ortho-alkylarenols via single electron transfer (SET) and the formation of o-QMs via hydrogen atom transfer (HAT).\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"1 1\",\"pages\":\"\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2024-12-26\",\"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.4c04494\",\"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.4c04494","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

本文报道了通过无金属可见光诱导的邻烷基烯醇氧化生成邻醌类化合物（o-QMs），以及它们随后与烯烃反应生成铬，收率可达91%。其关键是通过单电子转移（SET）选择性激活邻烷基烯醇的苯基C(sp3) -H键，并通过氢原子转移（HAT）形成o-QMs。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction

查看原文本刊更多论文

Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction

Reported herein is the generation of ortho-quinone methides (o-QMs) via metal-free visible-light-induced oxidation of ortho-alkylarenols, as well as their subsequent reaction with olefins to afford chromans in good to excellent yields (up to 91%). The key is the selective activation of the benzylic C(sp³)–H bond of ortho-alkylarenols via single electron transfer (SET) and the formation of o-QMs via hydrogen atom transfer (HAT).

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.