单碳合成物 CH3CN 的直接 C-C 键裂解:通过电化学氧化合成吡咯并[1,2-a]喹喔啉类化合物

IF 4.4 2区 化学 Q2 CHEMISTRY, APPLIED
Fengkai Sun , Man Miao , Wenxue Li , Xiao‐Bing Lan , Jian‐Qiang Yu , Jian Zhang , Zhenyu An
{"title":"单碳合成物 CH3CN 的直接 C-C 键裂解:通过电化学氧化合成吡咯并[1,2-a]喹喔啉类化合物","authors":"Fengkai Sun ,&nbsp;Man Miao ,&nbsp;Wenxue Li ,&nbsp;Xiao‐Bing Lan ,&nbsp;Jian‐Qiang Yu ,&nbsp;Jian Zhang ,&nbsp;Zhenyu An","doi":"10.1002/adsc.202400886","DOIUrl":null,"url":null,"abstract":"<div><div>A direct electrochemical redox reaction involving radical cross‐coupling cyclization for the synthesis of pyrrolo[1,2‐<em>a</em>]quinoxaline derivatives from 1‐(2‐aminophenyl)pyrroles and CH<sub>3</sub>CN has been developed, which includes the functionalization of C(<em>sp</em><sup>3</sup>)−H bonds as well as the construction of C−C and C−N bonds. Notably, the control and deuterium‐labelling experiments suggest that CH<sub>3</sub>CN in this reaction acts as both a carbon source <em>via</em> C−C cleavage and solvent. The reaction features metal‐ and oxidant‐free conditions, and various substituted pyrrolo[1,2‐<em>a</em>]quinoxaline derivatives were obtained.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4649-4653"},"PeriodicalIF":4.4000,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Direct C−C Bond Cleavage of CH3CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation\",\"authors\":\"Fengkai Sun ,&nbsp;Man Miao ,&nbsp;Wenxue Li ,&nbsp;Xiao‐Bing Lan ,&nbsp;Jian‐Qiang Yu ,&nbsp;Jian Zhang ,&nbsp;Zhenyu An\",\"doi\":\"10.1002/adsc.202400886\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A direct electrochemical redox reaction involving radical cross‐coupling cyclization for the synthesis of pyrrolo[1,2‐<em>a</em>]quinoxaline derivatives from 1‐(2‐aminophenyl)pyrroles and CH<sub>3</sub>CN has been developed, which includes the functionalization of C(<em>sp</em><sup>3</sup>)−H bonds as well as the construction of C−C and C−N bonds. Notably, the control and deuterium‐labelling experiments suggest that CH<sub>3</sub>CN in this reaction acts as both a carbon source <em>via</em> C−C cleavage and solvent. The reaction features metal‐ and oxidant‐free conditions, and various substituted pyrrolo[1,2‐<em>a</em>]quinoxaline derivatives were obtained.</div></div>\",\"PeriodicalId\":118,\"journal\":{\"name\":\"Advanced Synthesis & Catalysis\",\"volume\":\"366 22\",\"pages\":\"Pages 4649-4653\"},\"PeriodicalIF\":4.4000,\"publicationDate\":\"2024-11-19\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Advanced Synthesis & Catalysis\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1615415024005223\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1615415024005223","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0

摘要

研究人员开发了一种直接电化学氧化还原反应,该反应涉及自由基交叉耦合环化,用于从 1-(2-氨基苯基)吡咯和 CH3CN 合成吡咯并[1,2-a]喹喔啉衍生物,其中包括 C(sp3)-H 键的官能化以及 C-C 和 C-N 键的构建。值得注意的是,对照和氘标记实验表明,CH3CN 在该反应中通过 C-C 裂解既是碳源,又是溶剂。该反应以无金属和氧化剂条件为特征,并获得了各种取代的吡咯并[1,2-a]喹喔啉衍生物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Direct C−C Bond Cleavage of CH3CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation

Direct C−C Bond Cleavage of CH3CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation
A direct electrochemical redox reaction involving radical cross‐coupling cyclization for the synthesis of pyrrolo[1,2‐a]quinoxaline derivatives from 1‐(2‐aminophenyl)pyrroles and CH3CN has been developed, which includes the functionalization of C(sp3)−H bonds as well as the construction of C−C and C−N bonds. Notably, the control and deuterium‐labelling experiments suggest that CH3CN in this reaction acts as both a carbon source via C−C cleavage and solvent. The reaction features metal‐ and oxidant‐free conditions, and various substituted pyrrolo[1,2‐a]quinoxaline derivatives were obtained.
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
Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis 化学-应用化学
CiteScore
9.40
自引率
7.40%
发文量
447
审稿时长
1.8 months
期刊介绍: Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
×
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