镍/光氧化还原双催化1,3-丁二烯选择性烷基芳基化双官能化

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC
Aidana Gimnkhan, Rajesh Kancherla, Krishnamoorthy Muralirajan* and Magnus Rueping*, 
{"title":"镍/光氧化还原双催化1,3-丁二烯选择性烷基芳基化双官能化","authors":"Aidana Gimnkhan,&nbsp;Rajesh Kancherla,&nbsp;Krishnamoorthy Muralirajan* and Magnus Rueping*,&nbsp;","doi":"10.1021/acs.orglett.5c0151810.1021/acs.orglett.5c01518","DOIUrl":null,"url":null,"abstract":"<p >Photocatalytic multicomponent reactions are at the forefront of organic synthesis. In recent years, the dicarbofunctionalization of olefins has received significant attention, with nickel serving as a key transition metal catalyst under photochemical conditions. However, achieving regioselective 1,4-alkylarylation of dienes with alkyl and aryl bromides remains challenging. In this work, we present a Ni/photoredox dual catalysis approach for the regioselective alkylarylation of dienes, offering a mild reaction that eliminates the need for stochiometric metal reductants. Broad substrate scope and mechanistic investigations are presented that support the proposed reaction mechanism.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 21","pages":"5509–5514 5509–5514"},"PeriodicalIF":5.0000,"publicationDate":"2025-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Selective Alkylarylation Difunctionalization of 1,3-Butadienes via Nickel/Photoredox Dual Catalysis\",\"authors\":\"Aidana Gimnkhan,&nbsp;Rajesh Kancherla,&nbsp;Krishnamoorthy Muralirajan* and Magnus Rueping*,&nbsp;\",\"doi\":\"10.1021/acs.orglett.5c0151810.1021/acs.orglett.5c01518\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Photocatalytic multicomponent reactions are at the forefront of organic synthesis. In recent years, the dicarbofunctionalization of olefins has received significant attention, with nickel serving as a key transition metal catalyst under photochemical conditions. However, achieving regioselective 1,4-alkylarylation of dienes with alkyl and aryl bromides remains challenging. In this work, we present a Ni/photoredox dual catalysis approach for the regioselective alkylarylation of dienes, offering a mild reaction that eliminates the need for stochiometric metal reductants. Broad substrate scope and mechanistic investigations are presented that support the proposed reaction mechanism.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 21\",\"pages\":\"5509–5514 5509–5514\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-05-19\",\"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.5c01518\",\"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.5c01518","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

光催化多组分反应是有机合成的前沿。近年来,烯烃的二碳官能化反应受到了广泛的关注,其中镍作为光化学条件下关键的过渡金属催化剂。然而,实现二烯与烷基和芳基溴的区域选择性1,4-烷基芳基化仍然具有挑战性。在这项工作中,我们提出了一种镍/光氧化还原双催化方法,用于二烯的区域选择性烷基化,提供了一个温和的反应,消除了对化学计量金属还原剂的需要。广泛的底物范围和机理研究提出了支持所提出的反应机理。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Selective Alkylarylation Difunctionalization of 1,3-Butadienes via Nickel/Photoredox Dual Catalysis

Selective Alkylarylation Difunctionalization of 1,3-Butadienes via Nickel/Photoredox Dual Catalysis

Photocatalytic multicomponent reactions are at the forefront of organic synthesis. In recent years, the dicarbofunctionalization of olefins has received significant attention, with nickel serving as a key transition metal catalyst under photochemical conditions. However, achieving regioselective 1,4-alkylarylation of dienes with alkyl and aryl bromides remains challenging. In this work, we present a Ni/photoredox dual catalysis approach for the regioselective alkylarylation of dienes, offering a mild reaction that eliminates the need for stochiometric metal reductants. Broad substrate scope and mechanistic investigations are presented that support the proposed reaction 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