Excited Pd-catalyzed dearomative 1,4-dicarbofunctionalization of nonactivated aromatic rings†

Kai Jiang , Ziyan Zhao , Xiaodong Yin , Fangjun Chen , Biaolin Yin
{"title":"Excited Pd-catalyzed dearomative 1,4-dicarbofunctionalization of nonactivated aromatic rings†","authors":"Kai Jiang ,&nbsp;Ziyan Zhao ,&nbsp;Xiaodong Yin ,&nbsp;Fangjun Chen ,&nbsp;Biaolin Yin","doi":"10.1039/d4qo02173h","DOIUrl":null,"url":null,"abstract":"<div><div>Excited-palladium catalysis has already been exploited to achieve 1,4-difunctionalization of dienes <em>via</em> the radical generation of an allylpalladium intermediate. Herein, nonactivated phenyl rings, which can be treated as masked trienes, have accomplished dearomative 1,4-dicarbofunctionalization in an excited-palladium catalyzed two- or three-component reaction system. A wide range of alkyl bromides and 1,3-dicarbonyl compounds, playing the roles of radical precursors and nucleophiles, respectively, were found to be suitable for this reaction. Various three-dimensional molecular architectures with multiple quaternary carbon centers were efficiently constructed by means of this mild reaction.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1579-1585"},"PeriodicalIF":0.0000,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S205241292500004X","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

Abstract

Excited-palladium catalysis has already been exploited to achieve 1,4-difunctionalization of dienes via the radical generation of an allylpalladium intermediate. Herein, nonactivated phenyl rings, which can be treated as masked trienes, have accomplished dearomative 1,4-dicarbofunctionalization in an excited-palladium catalyzed two- or three-component reaction system. A wide range of alkyl bromides and 1,3-dicarbonyl compounds, playing the roles of radical precursors and nucleophiles, respectively, were found to be suitable for this reaction. Various three-dimensional molecular architectures with multiple quaternary carbon centers were efficiently constructed by means of this mild reaction.

Abstract Image

激发pd催化非活化芳香环的1,4-二碳功能化
激发钯催化已经被用于通过自由基生成烯基钯中间体来实现二烯的1,4-二官能化。在本研究中,非活化苯基环被处理为蒙面三烯,在激发钯催化的二组分和三组分体系中完成了去芳香1,4-二碳功能化。广泛的烷基溴和1,3-二羰基化合物分别扮演自由基前体和亲核试剂的角色,适合于该反应。通过这种温和的反应,有效地构建了多种具有多个季碳中心的三维分子结构。
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
7.80
自引率
0.00%
发文量
0
×
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:481959085
Book学术官方微信