Alkylated Quinolines through Benzylic sp3 C−H Functionalization: Sequential Synthesis and Photophysical Studies

IF 2.7 4区 化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2024-12-05 DOI:10.1002/ajoc.202400607
Sundararajan Suresh, Pari Keerthana, Prof. Dr. Fazlurrahman Nawaz Khan
{"title":"Alkylated Quinolines through Benzylic sp3 C−H Functionalization: Sequential Synthesis and Photophysical Studies","authors":"Sundararajan Suresh,&nbsp;Pari Keerthana,&nbsp;Prof. Dr. Fazlurrahman Nawaz Khan","doi":"10.1002/ajoc.202400607","DOIUrl":null,"url":null,"abstract":"<p>An efficient method has been developed for the green synthesis of alkylated quinolines <i>via</i> Cu-TEMPO catalyzed dehydrogenation, and DEP/DES-assisted benzylic C−H functionalization followed by cross Rauhut-Currier type reaction. The reaction mechanism is elucidated through control experiments and <sup>1</sup>H NMR reaction monitoring. This transformation offers several advantages, including moderate to good yields of the desired products, mild reaction conditions, use of a cost-effective metal catalyst, good functional group tolerance, and applicability to gram-scale synthesis. Additionally, the synthetic utility and the photophysical properties of the synthesized alkylated quinoline derivatives were investigated.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 2","pages":""},"PeriodicalIF":2.7000,"publicationDate":"2024-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Asian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://aces.onlinelibrary.wiley.com/doi/10.1002/ajoc.202400607","RegionNum":4,"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

An efficient method has been developed for the green synthesis of alkylated quinolines via Cu-TEMPO catalyzed dehydrogenation, and DEP/DES-assisted benzylic C−H functionalization followed by cross Rauhut-Currier type reaction. The reaction mechanism is elucidated through control experiments and 1H NMR reaction monitoring. This transformation offers several advantages, including moderate to good yields of the desired products, mild reaction conditions, use of a cost-effective metal catalyst, good functional group tolerance, and applicability to gram-scale synthesis. Additionally, the synthetic utility and the photophysical properties of the synthesized alkylated quinoline derivatives were investigated.

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
苯基sp3 C−H功能化的烷基化喹啉:顺序合成和光物理研究
通过Cu-TEMPO催化脱氢,DEP/ des辅助C - H官能化,然后进行交叉罗hut- currier型反应,建立了一种绿色合成烷基化喹啉的高效方法。通过对照实验和1H NMR反应监测,阐明了反应机理。这种转化有几个优点,包括所需产物的产率适中,反应条件温和,使用成本低廉的金属催化剂,良好的官能团耐受性,以及适用于克级合成。此外,还对合成的烷基化喹啉衍生物的合成效用和光物理性质进行了研究。
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
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
期刊最新文献
Hypervalent Iodine(III)-Mediated Oxidative Degradation of 2-Alkoxychalcones Under Copper(II) Catalysis for the Synthesis of Unsymmetrical 1,2-Diaryl Diketones Metal–free Pathway to α-Fluoro-α-nitrohomopropargylic Amides Employing Alkynyliodonium Salts Palladium-Catalyzed Asymmetric [3+2] Cyclization for the Synthesis of Chiral 2,3-dihydrofuran Regulated by the Side-Arm Effect of diSaBOX Ligands A Comprehensive Review for the Straightforward Preparation of Trifluoromethylated Internal Alkynes Recent Advances in Asymmetric Catalytic Annulation of γ- and δ-Hydroxy-α,β-Unsaturated Carbonyl Compounds for the Synthesis of Chiral Oxygen Heterocycles
×
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