• 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

Polarclean/水作为钯/碳催化吲哚选择性C2-芳基化反应的安全且可回收介质

Polarclean/Water as a Safe and Recoverable Medium for Selective C2-Arylation of Indoles Catalyzed by Pd/C.

作者信息

Campana Filippo, Massaccesi Beatrice Maria, Santoro Stefano, Piermatti Oriana, Vaccaro Luigi

机构信息

Laboratory of Green S.O.C. - Dipartimento di Chimica, biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, 06123 Perugia - I, Italy.

出版信息

ACS Sustain Chem Eng. 2020 Nov 9;8(44):16441-16450. doi: 10.1021/acssuschemeng.0c05049. Epub 2020 Oct 27.

DOI:10.1021/acssuschemeng.0c05049
PMID:33828930
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8018292/
Abstract

Herein, we report the use of nontoxic, water-miscible Polarclean as a safe dipolar aprotic solvent for the metal-catalyzed direct C2-H arylation of indoles using Pd/C as a catalyst. The developed method allows reaching excellent yields and regioselectivities, and it tolerates various substituents on both indole and diaryliodonium salt scaffolds. Polarclean is fully recoverable and reusable; it shows a very low leaching of the metal catalyst, allowing its complete recovery and reuse for at least six representative reaction runs.

摘要

在此，我们报道了使用无毒、与水混溶的Polarclean作为一种安全的偶极非质子溶剂，以钯/碳作为催化剂，用于吲哚的金属催化直接C2-H芳基化反应。所开发的方法能够实现优异的产率和区域选择性，并且对吲哚和二芳基碘鎓盐骨架上的各种取代基均具有耐受性。Polarclean可完全回收并重复使用；它显示出金属催化剂的浸出率非常低，能够将其完全回收并重复使用至少六次代表性反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c93/8018292/49c0d0e85c83/sc0c05049_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c93/8018292/6fcb829323d0/sc0c05049_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c93/8018292/f5e2cf960728/sc0c05049_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c93/8018292/204be40d1c0d/sc0c05049_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c93/8018292/15b393879ad9/sc0c05049_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c93/8018292/49c0d0e85c83/sc0c05049_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c93/8018292/6fcb829323d0/sc0c05049_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c93/8018292/f5e2cf960728/sc0c05049_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c93/8018292/204be40d1c0d/sc0c05049_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c93/8018292/15b393879ad9/sc0c05049_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0c93/8018292/49c0d0e85c83/sc0c05049_0005.jpg

相似文献

1
Polarclean/Water as a Safe and Recoverable Medium for Selective C2-Arylation of Indoles Catalyzed by Pd/C.Polarclean/水作为钯/碳催化吲哚选择性C2-芳基化反应的安全且可回收介质
ACS Sustain Chem Eng. 2020 Nov 9;8(44):16441-16450. doi: 10.1021/acssuschemeng.0c05049. Epub 2020 Oct 27.
2
C2-H Arylation of Indoles Catalyzed by Palladium-Containing Metal-Organic-Framework in γ-Valerolactone.钯基金属有机框架在γ-戊内酯中催化吲哚的 C2-H 芳基化反应。
ChemSusChem. 2020 May 22;13(10):2786-2791. doi: 10.1002/cssc.202000378. Epub 2020 Mar 18.
3
C-2 selective arylation of indoles with heterogeneous nanopalladium and diaryliodonium salts.吲哚与非均相纳米钯和二芳基碘鎓盐的C-2选择性芳基化反应。
Chemistry. 2014 Oct 13;20(42):13531-5. doi: 10.1002/chem.201404017. Epub 2014 Aug 28.
4
Polarclean as a Sustainable Reaction Medium for the Waste Minimized Synthesis of Heterocyclic Compounds.Polarclean作为用于杂环化合物最小化废弃物合成的可持续反应介质。
Front Chem. 2019 Jan 29;6:659. doi: 10.3389/fchem.2018.00659. eCollection 2018.
5
Palladium nanoparticles encapsulated in a metal-organic framework as efficient heterogeneous catalysts for direct C2 arylation of indoles.负载在金属有机骨架中的钯纳米颗粒作为高效非均相催化剂用于吲哚的直接 C2 芳基化反应。
Chemistry. 2011 Nov 4;17(45):12706-12. doi: 10.1002/chem.201101705. Epub 2011 Sep 28.
6
Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions.铜（II）催化吲哚在温和条件下的直接和位点选择性芳基化反应。
J Am Chem Soc. 2008 Jul 2;130(26):8172-4. doi: 10.1021/ja801767s. Epub 2008 Jun 11.
7
Expeditious and Solvent-Free Nickel-Catalyzed C-H Arylation of Arenes and Indoles.快速、无溶剂镍催化芳烃和吲哚的 C-H 芳基化反应。
ChemSusChem. 2017 May 22;10(10):2242-2248. doi: 10.1002/cssc.201700321. Epub 2017 Apr 18.
8
On the Barton Copper-Catalyzed C3-Arylation of Indoles using Triarylbismuth bis(trifluoroacetate) Reagents.关于使用三芳基铋双（三氟乙酸酯）试剂进行的巴顿铜催化吲哚的C3-芳基化反应
Chempluschem. 2023 Aug;88(8):e202200465. doi: 10.1002/cplu.202200465. Epub 2023 Mar 15.
9
Palladium-catalyzed direct C2 arylation of N-substituted indoles with 1-aryltriazenes.钯催化的N-取代吲哚与1-芳基三氮烯的直接C2芳基化反应。
Chem Asian J. 2014 Sep;9(9):2584-9. doi: 10.1002/asia.201402274. Epub 2014 Jun 11.
10
Microwave-accelerated Pd-catalyzed desulfitative direct C2-arylation of free (NH)-indoles with arylsulfinic acids.微波促进的 Pd 催化的游离（NH）吲哚的脱硫直接 C2-芳基化反应与芳基亚磺酸。
Chem Asian J. 2013 Dec;8(12):3185-90. doi: 10.1002/asia.201300913. Epub 2013 Sep 2.

引用本文的文献

1
A Waste-Minimized Approach to Cassar-Heck Reaction Based on POLITAG-Pd Heterogeneous Catalyst and Recoverable Acetonitrile Azeotrope.基于 POLITAG-Pd 负载型催化剂和可回收乙腈共沸物的卡塞尔-赫克反应的废物最小化方法。
ChemSusChem. 2021 Aug 23;14(16):3359-3366. doi: 10.1002/cssc.202101052. Epub 2021 Jul 22.

本文引用的文献

1
C2-H Arylation of Indoles Catalyzed by Palladium-Containing Metal-Organic-Framework in γ-Valerolactone.钯基金属有机框架在γ-戊内酯中催化吲哚的 C2-H 芳基化反应。
ChemSusChem. 2020 May 22;13(10):2786-2791. doi: 10.1002/cssc.202000378. Epub 2020 Mar 18.
2
Recent Advances on the C2-Functionalization of Indole via Umpolung.吲哚 C2-功能化的最新进展：反转策略
Top Curr Chem (Cham). 2020 Feb 7;378(2):22. doi: 10.1007/s41061-020-0287-7.
3
C-H functionalization reactions under flow conditions.流动条件下的碳-氢官能团化反应。
Chem Soc Rev. 2019 May 20;48(10):2767-2782. doi: 10.1039/c8cs00211h.
4
Polarclean as a Sustainable Reaction Medium for the Waste Minimized Synthesis of Heterocyclic Compounds.Polarclean作为用于杂环化合物最小化废弃物合成的可持续反应介质。
Front Chem. 2019 Jan 29;6:659. doi: 10.3389/fchem.2018.00659. eCollection 2018.
5
3d Transition Metals for C-H Activation.用于 C-H 活化的 3d 过渡金属。
Chem Rev. 2019 Feb 27;119(4):2192-2452. doi: 10.1021/acs.chemrev.8b00507. Epub 2018 Nov 27.
6
Recent applications of C-H functionalization in complex natural product synthesis.C-H 功能化在复杂天然产物合成中的最新应用。
Chem Soc Rev. 2018 Dec 7;47(23):8925-8967. doi: 10.1039/c8cs00716k. Epub 2018 Nov 14.
7
Enantioselective C2-Alkylation of Indoles through a Redox-Relay Heck Reaction of 2-Indole Triflates.通过 2-吲哚三氟甲磺酸酯的氧化还原接力 Heck 反应实现吲哚的对映选择性 C2-烷基化反应。
Chemistry. 2019 Jan 7;25(2):512-515. doi: 10.1002/chem.201805416. Epub 2018 Dec 11.
8
Investigation of the Use of a Bio-Derived Solvent for Non-Solvent-Induced Phase Separation (NIPS) Fabrication of Polysulfone Membranes.用于聚砜膜非溶剂诱导相分离（NIPS）制备的生物衍生溶剂的应用研究。
Membranes (Basel). 2018 May 7;8(2):23. doi: 10.3390/membranes8020023.
9
Towards Sustainable C-H Functionalization Reactions: The Emerging Role of Bio-Based Reaction Media.迈向可持续的 C-H 功能化反应：生物基反应介质的新兴作用。
Chemistry. 2018 Sep 12;24(51):13383-13390. doi: 10.1002/chem.201801114. Epub 2018 Jun 20.
10
Direct C2-Functionalization of Indoles Triggered by the Generation of Iminium Species from Indole and Sulfonium Salt.由吲哚和锍盐生成亚胺离子引发的吲哚直接C2官能团化反应
Chemistry. 2017 Aug 10;23(45):10925-10930. doi: 10.1002/chem.201702338. Epub 2017 Jul 20.