1,3-二酮与芳基烯烃和水的碳-碳键裂解重排电化学氧化重组

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-25 DOI:10.1021/acs.orglett.5c00929

Wei Wu, Rongxing Linghu, Bingjie Jian, Jun Shi, Qin Chi, Biaobiao Jiang, Hai Ren

{"title":"1,3-二酮与芳基烯烃和水的碳-碳键裂解重排电化学氧化重组","authors":"Wei Wu, Rongxing Linghu, Bingjie Jian, Jun Shi, Qin Chi, Biaobiao Jiang, Hai Ren","doi":"10.1021/acs.orglett.5c00929","DOIUrl":null,"url":null,"abstract":"We report the electrochemical cleavage and reassembly of 1,3-diketones with aryl alkenes and water for the synthesis of 1,4-ketoalcohol derivatives. This approach represents the first example of formal carbon–carbon cleavage of 1,3-diketones and alkene insertion via electro-oxidation, enabling the direct synthesis of diverse 1,4-ketoalcohol derivatives in good to high yields. The developed strategy employs an electrochemical approach using inexpensive commercial carbon electrodes in an undivided cell under mild and operationally simple conditions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"2 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Electrochemical Oxidative Reassembly of 1,3-Diketones with Aryl Alkenes and Water via Carbon–Carbon Bond Cleavage Rearrangement\",\"authors\":\"Wei Wu, Rongxing Linghu, Bingjie Jian, Jun Shi, Qin Chi, Biaobiao Jiang, Hai Ren\",\"doi\":\"10.1021/acs.orglett.5c00929\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"We report the electrochemical cleavage and reassembly of 1,3-diketones with aryl alkenes and water for the synthesis of 1,4-ketoalcohol derivatives. This approach represents the first example of formal carbon–carbon cleavage of 1,3-diketones and alkene insertion via electro-oxidation, enabling the direct synthesis of diverse 1,4-ketoalcohol derivatives in good to high yields. The developed strategy employs an electrochemical approach using inexpensive commercial carbon electrodes in an undivided cell under mild and operationally simple conditions.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"2 1\",\"pages\":\"\"},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2025-04-25\",\"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.5c00929\",\"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.5c00929","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

我们报道了1,3-二酮与芳基烯烃和水的电化学裂解和重组，以合成1,4-酮醇衍生物。这种方法代表了通过电氧化对1,3-二酮和烯烃插入进行正式碳-碳裂解的第一个例子，使各种1,4-酮醇衍生物的直接合成具有良好到高的收率。开发的策略采用电化学方法，在温和和操作简单的条件下，在未分裂的电池中使用廉价的商业碳电极。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Electrochemical Oxidative Reassembly of 1,3-Diketones with Aryl Alkenes and Water via Carbon–Carbon Bond Cleavage Rearrangement

查看原文本刊更多论文

Electrochemical Oxidative Reassembly of 1,3-Diketones with Aryl Alkenes and Water via Carbon–Carbon Bond Cleavage Rearrangement

We report the electrochemical cleavage and reassembly of 1,3-diketones with aryl alkenes and water for the synthesis of 1,4-ketoalcohol derivatives. This approach represents the first example of formal carbon–carbon cleavage of 1,3-diketones and alkene insertion via electro-oxidation, enabling the direct synthesis of diverse 1,4-ketoalcohol derivatives in good to high yields. The developed strategy employs an electrochemical approach using inexpensive commercial carbon electrodes in an undivided cell under mild and operationally simple conditions.

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.