金催化烯烃1,2-羧基化反应

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC
Tanmayee Nanda, Avishek Das, Prafulla Bera and Nitin T. Patil*, 
{"title":"金催化烯烃1,2-羧基化反应","authors":"Tanmayee Nanda,&nbsp;Avishek Das,&nbsp;Prafulla Bera and Nitin T. Patil*,&nbsp;","doi":"10.1021/acs.orglett.5c0028810.1021/acs.orglett.5c00288","DOIUrl":null,"url":null,"abstract":"<p >Herein, we disclose an unprecedented gold-catalyzed 1,2-carboxyarylation of alkenes through ligand-enabled Au(I)/Au(III) catalysis. Unlike other approaches for the arylative functionalization of C–C multiple bonds, attempts to utilize weak nucleophiles such as carboxylate anions were unsuccessful. The key to achieving this transformation is the use of a 1,3-diketone-appended alkene, which undergoes gold-catalyzed oxyarylation followed by retro-aldol reaction to afford the product. Detailed mechanistic investigations were conducted to support the proposed mechanism.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 9","pages":"2228–2234 2228–2234"},"PeriodicalIF":5.0000,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Gold-Catalyzed 1,2-Carboxyarylation of Alkenes\",\"authors\":\"Tanmayee Nanda,&nbsp;Avishek Das,&nbsp;Prafulla Bera and Nitin T. Patil*,&nbsp;\",\"doi\":\"10.1021/acs.orglett.5c0028810.1021/acs.orglett.5c00288\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Herein, we disclose an unprecedented gold-catalyzed 1,2-carboxyarylation of alkenes through ligand-enabled Au(I)/Au(III) catalysis. Unlike other approaches for the arylative functionalization of C–C multiple bonds, attempts to utilize weak nucleophiles such as carboxylate anions were unsuccessful. The key to achieving this transformation is the use of a 1,3-diketone-appended alkene, which undergoes gold-catalyzed oxyarylation followed by retro-aldol reaction to afford the product. Detailed mechanistic investigations were conducted to support the proposed mechanism.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 9\",\"pages\":\"2228–2234 2228–2234\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-02-24\",\"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.5c00288\",\"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://pubs.acs.org/doi/10.1021/acs.orglett.5c00288","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

在此,我们通过配体激活Au(I)/Au(III)催化揭示了一种前所未有的金催化的1,2-羧基化烯烃。不同于其他的C-C多键芳化功能化方法,利用弱亲核试剂如羧酸阴离子的尝试是不成功的。实现这一转变的关键是使用1,3-二酮附加的烯烃,该烯烃经过金催化的氧化芳基化,然后进行反醛醇反应以获得产品。为了支持提议的机制,进行了详细的机制调查。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Gold-Catalyzed 1,2-Carboxyarylation of Alkenes

Gold-Catalyzed 1,2-Carboxyarylation of Alkenes

Herein, we disclose an unprecedented gold-catalyzed 1,2-carboxyarylation of alkenes through ligand-enabled Au(I)/Au(III) catalysis. Unlike other approaches for the arylative functionalization of C–C multiple bonds, attempts to utilize weak nucleophiles such as carboxylate anions were unsuccessful. The key to achieving this transformation is the use of a 1,3-diketone-appended alkene, which undergoes gold-catalyzed oxyarylation followed by retro-aldol reaction to afford the product. Detailed mechanistic investigations were conducted to support the proposed mechanism.

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
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.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信