Kharasch-Type Haloalkylation of Alkenes by Photoinduced Copper Catalysis.

IF 15.6 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Journal of the American Chemical Society Pub Date : 2025-06-04 Epub Date: 2025-05-20 DOI:10.1021/jacs.5c05699
Yuan Cai, Mahiob Dawor, Gaurav Gaurav, Tobias Ritter
{"title":"Kharasch-Type Haloalkylation of Alkenes by Photoinduced Copper Catalysis.","authors":"Yuan Cai, Mahiob Dawor, Gaurav Gaurav, Tobias Ritter","doi":"10.1021/jacs.5c05699","DOIUrl":null,"url":null,"abstract":"<p><p>The simultaneous construction of C-C and C-X bonds in a single step facilitates multistep synthesis through rapid carbon chain growth and subsequent transformations of halide functionalities. Traditional Kharasch addition requires simple polyhalogenated compounds or those with electron-withdrawing groups at the α-carbon. Herein, we present a Kharasch-type reaction utilizing a broad range of carboxylic acid-derived redox-active esters as the alkyl source, which enables the efficient introduction of highly functionalized alkyl groups. Our method produces α-halo carbonyls that enable versatile nucleophilic substitutions for synthesizing valuable compounds, such as unnatural α-amino acids.</p>","PeriodicalId":49,"journal":{"name":"Journal of the American Chemical Society","volume":" ","pages":"18438-18444"},"PeriodicalIF":15.6000,"publicationDate":"2025-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12147127/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the American Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/jacs.5c05699","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/5/20 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

Abstract

The simultaneous construction of C-C and C-X bonds in a single step facilitates multistep synthesis through rapid carbon chain growth and subsequent transformations of halide functionalities. Traditional Kharasch addition requires simple polyhalogenated compounds or those with electron-withdrawing groups at the α-carbon. Herein, we present a Kharasch-type reaction utilizing a broad range of carboxylic acid-derived redox-active esters as the alkyl source, which enables the efficient introduction of highly functionalized alkyl groups. Our method produces α-halo carbonyls that enable versatile nucleophilic substitutions for synthesizing valuable compounds, such as unnatural α-amino acids.

光诱导铜催化烃类的kharasch型卤化烷基化。
在一个步骤中同时构建C-C和C-X键,通过快速的碳链生长和随后的卤化物官能团转变,促进了多步合成。传统的Kharasch加成法需要简单的多卤化化合物或在α-碳上具有吸电子基团的化合物。在这里,我们提出了一个kharasch型反应,利用广泛的羧酸衍生的氧化还原活性酯作为烷基源,这使得高效地引入高官能团烷基。我们的方法产生α-光环羰基,使合成有价值的化合物(如非天然α-氨基酸)的多功能亲核取代成为可能。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
CiteScore
24.40
自引率
6.00%
发文量
2398
审稿时长
1.6 months
期刊介绍: The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.
×
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