Merging 2,3-butanedione and N-hydroxysuccinimide as visible-light-enabled hydrogen atom transfer catalysts for CC double bond cleavage of 2-cyanoaryl acrylamides toward the synthesis of 4-amino-2-quinolones†

IF 4.6 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Chemistry Frontiers Pub Date : 2024-05-20 DOI:10.1039/D4QO00458B
Jun Huang, Fengting Zhu, Jinlian Wen, Jiali Xu, Jing-Mei Yuan and Wenqiang Chen
{"title":"Merging 2,3-butanedione and N-hydroxysuccinimide as visible-light-enabled hydrogen atom transfer catalysts for CC double bond cleavage of 2-cyanoaryl acrylamides toward the synthesis of 4-amino-2-quinolones†","authors":"Jun Huang, Fengting Zhu, Jinlian Wen, Jiali Xu, Jing-Mei Yuan and Wenqiang Chen","doi":"10.1039/D4QO00458B","DOIUrl":null,"url":null,"abstract":"<p >The C<img>C double bond cleavage of 2-cyanoaryl acrylamides through merging 2,3-butanedione and <em>N</em>-hydroxysuccinimide as visible-light-enabled hydrogen atom transfer catalysts is effectively established for generating functionalized 4-amino-2-quinolones under metal-free and redox neutral conditions. Detailed mechanism studies indicate that the solvent 1,3-dioxolane offers the crucial 1,3-dioxolan-2-yl radical facilitated by the <em>in situ</em> formed H-atom abstracting species, and 2-alkenyl-1,3-dioxolane is probably another product in this photocatalytic protocol.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo00458b","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

Abstract

The CC double bond cleavage of 2-cyanoaryl acrylamides through merging 2,3-butanedione and N-hydroxysuccinimide as visible-light-enabled hydrogen atom transfer catalysts is effectively established for generating functionalized 4-amino-2-quinolones under metal-free and redox neutral conditions. Detailed mechanism studies indicate that the solvent 1,3-dioxolane offers the crucial 1,3-dioxolan-2-yl radical facilitated by the in situ formed H-atom abstracting species, and 2-alkenyl-1,3-dioxolane is probably another product in this photocatalytic protocol.

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
将 2,3-丁二酮和 N-羟基琥珀酰亚胺合并为可见光驱动的氢原子转移催化剂,用于从 2-氰基芳香族丙烯酰胺到 4-氨基-2-喹啉酮的 C=C 双键裂解反应
在无金属和氧化还原中性条件下,通过合并 2,3-丁二酮和 N-羟基琥珀酰亚胺作为可见光驱动的氢原子转移催化剂,有效地建立了 2-氰基芳基丙烯酰胺的 C=C 双键裂解,从而生成功能化的 4-氨基-2-喹啉酮。详细的机理研究表明,溶剂 1,3-二氧戊环在原位形成的氢原子抽取物种的促进下提供了关键的 1,3-二氧戊环-2-基自由基,而 2-烯基-1,3-二氧戊环可能是该光催化方案中的另一种产物。
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
Organic Chemistry Frontiers
Organic Chemistry Frontiers CHEMISTRY, ORGANIC-
CiteScore
7.90
自引率
11.10%
发文量
686
审稿时长
1 months
期刊介绍: Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
期刊最新文献
A Ligand-assisted Manganese-enabled Direct C-H Difluoromethylation of Arenes Photoredox-Enabled Ring-Opening of Cyclobutanes via the Formation of a Carbon Radical Asymmetric Synthesis of 1H-pyrazolo[3,4-b]pyridine Analogues Catalyzed by Chiral-at-Metal Rh(III) Complexes Total Synthesis of (‒)-Deglycocadambine Copper-Catalyzed Allenynylative C–P Couplings of Diynylic Acetates with Hydrophosphoryl Compounds Leading to Phosphorylated Allenynes
×
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
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:481959085
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