• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

在氯化胆碱:三乙醇胺这种可重复使用的低共熔溶剂中,实现高效的无碱和无配体钯催化酚类的芳基化反应。

Efficient base- and ligand-free palladium catalysed -arylation of phenols in choline chloride:triethanolamine as a reusable deep eutectic solvent.

作者信息

Abbasi Fatemeh, Sardarian Ali Reza

机构信息

Chemistry Department, College of Sciences, Shiraz University, Shiraz 71946-84795, Iran.

出版信息

R Soc Open Sci. 2024 Jun 5;11(6):240045. doi: 10.1098/rsos.240045. eCollection 2024 Jun.

DOI:10.1098/rsos.240045
PMID:39100160
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11295942/
Abstract

In this paper, we present a novel and sustainable approach using choline chloride:triethanolamine as a green, efficient and reusable deep eutectic solvent (DES) for Pd-catalysed -arylation reactions with Pd/BaSO (10%). By using the unique properties of DESs, we successfully achieved C-O bond formation without the need for additional solvents, bases and ligands. This solvent/catalyst system ([ChCl][TEA]) functioned as a dual catalyst and solvent system, enabling fast and environmentally friendly C-O bond formation from phenol derivatives and electron-deficient aryl halides, leading to remarkable yields under mild reaction conditions. To identify and characterize this DES, we employed differential scanning calorimetry, thermogravimetric analysis, Fourier-transform infrared spectroscopy, refractive index, viscosity, the potential of hydrogen (pH) and conductivity measurements. One of the remarkable advantages of this DES system is its exceptional stability. This solvent/catalyst system exhibited high stability throughout the reaction cycles, showing no significant loss of activity. As a result, this DES and catalyst (Pd/BaSO (10%)) can be easily recycled and re-used for up to three consecutive cycles, making it an economically and environmentally attractive option for organic reactions. Our approach offers several key benefits, including simple catalyst preparation, quick reaction times and excellent production efficiency.

摘要

在本文中,我们提出了一种新颖且可持续的方法,使用氯化胆碱:三乙醇胺作为绿色、高效且可重复使用的深共熔溶剂(DES),用于钯催化的苯酚衍生物与缺电子芳基卤化物的芳基化反应(钯负载量为10%的硫酸钡钯催化剂)。通过利用深共熔溶剂的独特性质,我们成功实现了碳 - 氧键的形成,无需额外的溶剂、碱和配体。这种溶剂/催化剂体系([ChCl][TEA])兼具双重功能,既作为催化剂又作为溶剂体系,能够在温和的反应条件下,使苯酚衍生物和缺电子芳基卤化物快速且环保地形成碳 - 氧键,从而获得显著的产率。为了鉴定和表征这种深共熔溶剂,我们采用了差示扫描量热法、热重分析、傅里叶变换红外光谱、折射率、粘度、氢离子电位(pH)和电导率测量。这种深共熔溶剂体系的显著优点之一是其卓越的稳定性。该溶剂/催化剂体系在整个反应循环中表现出高稳定性,活性没有明显损失。因此,这种深共熔溶剂和催化剂(10%的硫酸钡钯)可以轻松回收并重复使用多达三个连续循环,使其成为有机反应在经济和环境方面颇具吸引力的选择。我们的方法具有几个关键优势,包括催化剂制备简单、反应时间短和生产效率高。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/bf53cc827ade/rsos.240045.f006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/d2aa843525ce/rsos.240045.f007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/b8dba9f27a0b/rsos.240045.f008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/7d49776e3666/rsos.240045.f001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/2e993a5d9cd1/rsos.240045.f002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/2a5db85799d5/rsos.240045.f003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/5a24c0ec96b1/rsos.240045.f004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/2bb67827eda7/rsos.240045.f005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/889f884b6958/rsos.240045.f009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/bf53cc827ade/rsos.240045.f006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/d2aa843525ce/rsos.240045.f007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/b8dba9f27a0b/rsos.240045.f008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/7d49776e3666/rsos.240045.f001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/2e993a5d9cd1/rsos.240045.f002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/2a5db85799d5/rsos.240045.f003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/5a24c0ec96b1/rsos.240045.f004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/2bb67827eda7/rsos.240045.f005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/889f884b6958/rsos.240045.f009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3a9e/11295942/bf53cc827ade/rsos.240045.f006.jpg

相似文献

1
Efficient base- and ligand-free palladium catalysed -arylation of phenols in choline chloride:triethanolamine as a reusable deep eutectic solvent.在氯化胆碱:三乙醇胺这种可重复使用的低共熔溶剂中,实现高效的无碱和无配体钯催化酚类的芳基化反应。
R Soc Open Sci. 2024 Jun 5;11(6):240045. doi: 10.1098/rsos.240045. eCollection 2024 Jun.
2
Environmentally friendly and non-polluting solvent pretreatment of palm samples for polyphenol analysis using choline chloride deep eutectic solvents.使用氯化胆碱低共熔溶剂对棕榈样品进行环境友好且无污染的溶剂预处理以进行多酚分析。
J Chromatogr A. 2017 Apr 7;1492:1-11. doi: 10.1016/j.chroma.2017.02.036. Epub 2017 Feb 21.
3
Ligand-Free Copper-Catalyzed Ullmann-Type C-O Bond Formation in Non-Innocent Deep Eutectic Solvents under Aerobic Conditions.有氧条件下在非惰性深共熔溶剂中无配体铜催化的乌尔曼型碳-氧键形成反应
ChemSusChem. 2022 Jan 10;15(1):e202102211. doi: 10.1002/cssc.202102211. Epub 2021 Dec 6.
4
Ligand-Free Bioinspired Suzuki-Miyaura Coupling Reactions using Aryltrifluoroborates as Effective Partners in Deep Eutectic Solvents.在深共熔溶剂中使用芳基三氟硼酸盐作为有效反应物的无配体生物启发式铃木-宫浦偶联反应
ChemSusChem. 2018 Oct 11;11(19):3495-3501. doi: 10.1002/cssc.201801382. Epub 2018 Sep 5.
5
Extraction and separation of flavonoids from Malus hupehensis using high-speed countercurrent chromatography based on deep eutectic solvent.基于深共晶溶剂的高速逆流色谱法从平邑甜茶中提取和分离黄酮类化合物。
J Chromatogr A. 2021 Mar 29;1641:461998. doi: 10.1016/j.chroma.2021.461998. Epub 2021 Feb 12.
6
Preparation of a novel environmentally friendly hydrophobic deep eutectic solvent ChCl-THY and its application in removal of hexavalent chromium from aqueous solution.制备新型环保疏水性深共晶溶剂 ChCl-THY 及其在水溶液中六价铬去除中的应用。
Water Environ Res. 2021 Oct;93(10):2250-2260. doi: 10.1002/wer.1597. Epub 2021 Jun 22.
7
Assessing the compatibility of choline-based deep eutectic solvents for the structural stability and activity of cellulase: Enzyme sustain at high temperature.评估胆碱基深共熔溶剂对纤维素酶结构稳定性和活性的兼容性:高温下酶的维持。
Int J Biol Macromol. 2023 Sep 30;249:125988. doi: 10.1016/j.ijbiomac.2023.125988. Epub 2023 Jul 25.
8
Interpretation of the phenolation and structural changes of lignin in a novel ternary deep eutectic solvent.新型三元离子液体中木质素的酚化作用及结构变化的解析
Int J Biol Macromol. 2024 Apr;264(Pt 1):130475. doi: 10.1016/j.ijbiomac.2024.130475. Epub 2024 Feb 28.
9
Choline Chloride-Based Deep Eutectic Systems in Sequential Friedländer Reaction and Palladium-Catalyzed sp CH Functionalization of Methyl Ketones.基于氯化胆碱的低共熔体系在甲基酮的连续Friedländer反应及钯催化sp C-H官能化反应中的应用
ACS Omega. 2019 May 2;4(5):8046-8055. doi: 10.1021/acsomega.9b00310. eCollection 2019 May 31.
10
DFT study of interaction of Palladium Pd (n = 1-6) nanoparticles with deep eutectic solvents.钯Pd(n = 1 - 6)纳米颗粒与深共熔溶剂相互作用的密度泛函理论研究
J Mol Graph Model. 2022 Jan;110:108072. doi: 10.1016/j.jmgm.2021.108072. Epub 2021 Nov 9.

本文引用的文献

1
Catalysis with magnetically retrievable and recyclable nanoparticles layered with Pd(0) for C-C/C-O coupling in water.用于水中C-C/C-O偶联反应的负载Pd(0)的磁性可回收纳米颗粒催化作用
RSC Adv. 2020 Feb 11;10(11):6452-6459. doi: 10.1039/c9ra10618a. eCollection 2020 Feb 7.
2
Magnetization of graphene oxide nanosheets using nickel magnetic nanoparticles as a novel support for the fabrication of copper as a practical, selective, and reusable nanocatalyst in C-C and C-O coupling reactions.使用镍磁性纳米颗粒对氧化石墨烯纳米片进行磁化,以此作为一种新型载体,用于制备在C-C和C-O偶联反应中实用、选择性高且可重复使用的铜纳米催化剂。
RSC Adv. 2021 Jul 27;11(42):25867-25879. doi: 10.1039/d1ra03578a.
3
Diaryl Ether: A Privileged Scaffold for Drug and Agrochemical Discovery.
二芳基醚:药物和农用化学品发现的优势骨架。
J Agric Food Chem. 2020 Sep 16;68(37):9839-9877. doi: 10.1021/acs.jafc.0c03369. Epub 2020 Aug 29.
4
Potentials of Diphenyl Ether Scaffold as a Therapeutic Agent: A Review.二苯醚骨架作为治疗剂的潜力:综述。
Mini Rev Med Chem. 2019;19(17):1392-1406. doi: 10.2174/1389557519666190312150132.
5
Metal- and Phenol-Free Synthesis of Biaryl Ethers: Access to Dibenzobistriazolo-1,4,7-oxadiazonines and Vancomycin-Like Glyco-Macrocycles as Antibacterial Agents.无金属和酚的联芳醚合成:二苯并双[1,4,7]三唑并[1,5-a]氧杂二氮嗪和万古霉素类似糖大环作为抗菌剂的获得。
J Org Chem. 2018 Dec 21;83(24):14882-14893. doi: 10.1021/acs.joc.8b01631. Epub 2018 Nov 30.
6
The peculiar effect of water on ionic liquids and deep eutectic solvents.水对离子液体和深共晶溶剂的特殊影响。
Chem Soc Rev. 2018 Nov 26;47(23):8685-8720. doi: 10.1039/c8cs00325d.
7
Synthesis, SAR and molecular docking study of novel non-β-lactam inhibitors of TEM type β-lactamase.新型TEM型β-内酰胺酶非β-内酰胺抑制剂的合成、构效关系及分子对接研究
Bioorg Med Chem Lett. 2017 Apr 1;27(7):1588-1592. doi: 10.1016/j.bmcl.2017.02.025. Epub 2017 Feb 16.
8
Deep eutectic solvents (DESs) and their applications.深层共熔溶剂(DESs)及其应用。
Chem Rev. 2014 Nov 12;114(21):11060-82. doi: 10.1021/cr300162p. Epub 2014 Oct 10.
9
Synthesis and evaluation of new diaryl ether and quinoline hybrids as potential antiplasmodial and antimicrobial agents.新型二芳基醚与喹啉杂化物作为潜在抗疟和抗菌剂的合成与评价
Bioorg Med Chem Lett. 2014 Apr 1;24(7):1719-23. doi: 10.1016/j.bmcl.2014.02.044. Epub 2014 Feb 27.
10
Copper-assisted nickel catalyzed ligand-free C(sp2)-O cross-coupling of vinyl halides and phenols.铜辅助镍催化的无配体 C(sp2)-O 交叉偶联反应,用于乙烯基卤化物和酚类化合物。
Org Lett. 2014 Feb 21;16(4):1040-3. doi: 10.1021/ol500134p. Epub 2014 Feb 6.