Visible-Light-Mediated Three-Component Alkene 1,2-Alkylpyridylation Reaction Using Alkylboronic Acids as Radical Precursors for the Synthesis of 4-Alkylpyridines

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2025-03-03 DOI:10.1021/acs.joc.4c02600
Zi-Jun Lei, Yi-Jian Ma, Qian-Qian Fan, Zhi-Xiong Wu, Yi-Yang Zheng, Guoming Sun, Zi-Wei Xi, Chengshuo Shen, Yong-Miao Shen
{"title":"Visible-Light-Mediated Three-Component Alkene 1,2-Alkylpyridylation Reaction Using Alkylboronic Acids as Radical Precursors for the Synthesis of 4-Alkylpyridines","authors":"Zi-Jun Lei, Yi-Jian Ma, Qian-Qian Fan, Zhi-Xiong Wu, Yi-Yang Zheng, Guoming Sun, Zi-Wei Xi, Chengshuo Shen, Yong-Miao Shen","doi":"10.1021/acs.joc.4c02600","DOIUrl":null,"url":null,"abstract":"We report the photocatalyzed three-component alkene 1,2-alkylpyridylation reaction between alkylboronic acids, 4-cyanopyridine, and an olefin to achieve the pyridination and alkylation of the olefin and the synthesis of structurally diversified 4-alkylpyridines. The readily available and easily manipulated alkylboronic acids were used as alkyl radical precursors. The reactions take place under mild conditions with a broad substrate scope and are easy to scale up to gram level, and they are therefore of potential practical value for the synthesis and structural modification of biologically active alkylpyridine derivatives.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02600","RegionNum":2,"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

Abstract

We report the photocatalyzed three-component alkene 1,2-alkylpyridylation reaction between alkylboronic acids, 4-cyanopyridine, and an olefin to achieve the pyridination and alkylation of the olefin and the synthesis of structurally diversified 4-alkylpyridines. The readily available and easily manipulated alkylboronic acids were used as alkyl radical precursors. The reactions take place under mild conditions with a broad substrate scope and are easy to scale up to gram level, and they are therefore of potential practical value for the synthesis and structural modification of biologically active alkylpyridine derivatives.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
以烷基硼酸为自由基前体的可见光介导的三组分烯烃1,2-烷基吡啶化反应合成4-烷基吡啶
本文报道了烷基硼酸、4-氰吡啶和烯烃在光催化下的三组分烯烃1,2-烷基吡啶化反应,实现了烯烃的吡啶化和烷基化,合成了结构多样化的4-烷基吡啶。利用易获得、易操作的烷基硼酸作为烷基自由基前体。反应条件温和,底物范围广,易于扩大到克级,因此对生物活性烷基吡啶衍生物的合成和结构修饰具有潜在的实用价值。
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 去求助
来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
期刊最新文献
Issue Editorial Masthead Issue Publication Information Resolving a Sequential Post-Transition-State Bifurcation Mechanism in the Dimerization of 2,3-Diazacyclopentadienone Base-Catalyzed Hydrothiolation of Dehydroalanine Peptides Electrochemical Sulfenamide Synthesis Bypassing Gaseous Amines with Formamide Surrogates
×
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
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术
文献互助 智能选刊 最新文献 互助须知 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 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1