Application of Hydroxyaromatic Aldehydes in Ultra-Efficient and Metal-Free Photocatalytic E→Z Isomerization of Olefin.

IF 7.5 2区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY ChemSusChem Pub Date : 2024-11-05 DOI:10.1002/cssc.202401387
Chun-Xiu Liu, Yao Yao, Zi-Wen Zhou, Song Qin, Zhi-Peng Yu, Fei-Yan Tao, Wen-Dian Li, Xiao-Qi Yu, Na Wang
{"title":"Application of Hydroxyaromatic Aldehydes in Ultra-Efficient and Metal-Free Photocatalytic E→Z Isomerization of Olefin.","authors":"Chun-Xiu Liu, Yao Yao, Zi-Wen Zhou, Song Qin, Zhi-Peng Yu, Fei-Yan Tao, Wen-Dian Li, Xiao-Qi Yu, Na Wang","doi":"10.1002/cssc.202401387","DOIUrl":null,"url":null,"abstract":"<p><p>The strategy of photocatalyzed E→Z isomerization of olefins to access thermodynamically less stable Z-alkenes has recently received considerable attention. Here, we have discovered a sensitizer of hydroxyaromatic aldehyde that can rapidly achieve olefin E→Z isomerization under blue light irradiation. Notably, 2-hydroxybenzene-1,3,5-tricarbaldehyde, when assisted by blue light, can achieve efficient and selective conversion within just 5 minutes (Z/E=92 : 8). The reaction can be successfully scaled up to gram scale, and exhibits remarkable reactivity toward various derivatives of ethyl cinnamate (27 examples) and other olefins. Furthermore, the former can be directly cyclized by a hydroxyl derivative to produce 4-substituted coumarin. The prominent preponderance of this method includes being metal-free, efficient, convenient, no by-products and achieving high selectivity. Correlation of sensitizer triplet energy (E<sub>T</sub>) and preliminary mechanistic experiments indicate that the accomplishment of this reaction is based on the selective excitation mechanism.</p>","PeriodicalId":149,"journal":{"name":"ChemSusChem","volume":null,"pages":null},"PeriodicalIF":7.5000,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemSusChem","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/cssc.202401387","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

Abstract

The strategy of photocatalyzed E→Z isomerization of olefins to access thermodynamically less stable Z-alkenes has recently received considerable attention. Here, we have discovered a sensitizer of hydroxyaromatic aldehyde that can rapidly achieve olefin E→Z isomerization under blue light irradiation. Notably, 2-hydroxybenzene-1,3,5-tricarbaldehyde, when assisted by blue light, can achieve efficient and selective conversion within just 5 minutes (Z/E=92 : 8). The reaction can be successfully scaled up to gram scale, and exhibits remarkable reactivity toward various derivatives of ethyl cinnamate (27 examples) and other olefins. Furthermore, the former can be directly cyclized by a hydroxyl derivative to produce 4-substituted coumarin. The prominent preponderance of this method includes being metal-free, efficient, convenient, no by-products and achieving high selectivity. Correlation of sensitizer triplet energy (ET) and preliminary mechanistic experiments indicate that the accomplishment of this reaction is based on the selective excitation mechanism.

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
羟基芳醛在超高效无金属光催化 E→Z 烯烃异构化中的应用。
最近,光催化烯烃 E→Z 异构化以获得热力学稳定性较低的 Z-烯烃的策略受到了广泛关注。在这里,我们发现了一种羟基芳香醛敏化剂,它能在蓝光照射下快速实现烯烃的 E→Z 异构化。值得注意的是,2-羟基苯-1,3,5-三甲醛在蓝光辅助下可在短短 5 分钟内实现高效和选择性转化(Z/E=92:8)。该反应可成功放大到克级,并对肉桂酸乙酯的各种衍生物(27 个实例)和其他烯烃具有显著的反应活性。此外,前者可直接通过羟基衍生物环化生成 4-取代香豆素。这种方法具有无金属、高效、方便、无副产物和高选择性等突出优点。敏化剂三重态能量(ET)的相关性和初步的机理实验表明,该反应的完成是基于选择性激发机制。
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
ChemSusChem
ChemSusChem 化学-化学综合
CiteScore
15.80
自引率
4.80%
发文量
555
审稿时长
1.8 months
期刊介绍: ChemSusChem Impact Factor (2016): 7.226 Scope: Interdisciplinary journal Focuses on research at the interface of chemistry and sustainability Features the best research on sustainability and energy Areas Covered: Chemistry Materials Science Chemical Engineering Biotechnology
期刊最新文献
Improved Compatibility of α-NaMnO2 Cathodes at the Interface with Ionic Liquid Electrolytes. Versatile Separators Toward Advanced Lithium-Sulfur Batteries: Status, Recent Progress, Challenges and Perspective. Influence of F-Containing Materials on Perovskite Solar Cells. Promoting Water Oxidation by Proton Acceptable Groups Surrounding Catalyst on Electrode Surface. Sulfite-Assisted Acetate Conversion from CO Electroreduction.
×
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: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