• 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

钯催化 2,4-二氯吡啶 C-4 选择性偶联及合成用于活细胞成像的吡啶基染料。

Palladium-Catalyzed C-4 Selective Coupling of 2,4-Dichloropyridines and Synthesis of Pyridine-Based Dyes for Live-Cell Imaging.

机构信息

Department of Forensic Science, Oil-tea in Medical Health Care and Functional Product Development Engineering Research Center in Jiangxi, Gannan Medical University, 1 Yixueyuan Road, Ganzhou, Jiangxi 341000, China.

Department of Chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, China.

出版信息

J Org Chem. 2020 May 15;85(10):6498-6508. doi: 10.1021/acs.joc.0c00449. Epub 2020 May 4.

DOI:10.1021/acs.joc.0c00449
PMID:32329338
Abstract

An alternative process of Pd-catalyzed C-4 selective coupling of 2,4-dichloropyridines with boronic esters was developed, which afforded 24 examples of C-4 coupled pyridines in moderate to good yields. After further arylation, 21 examples of C-2, C-4 diarylated pyridines with a significant photophysical property were obtained, which were applied as pyridine-based dyes into live-cell imaging with good biocompatibility and low toxicity.

摘要

发展了一种钯催化的 2,4-二氯吡啶与硼酸酯 C-4 选择性偶联的替代方法,该方法以中等至良好的收率得到了 24 个 C-4 偶联吡啶的实例。进一步芳基化后,得到了 21 个具有显著光物理性质的 C-2、C-4 二芳基吡啶的实例,这些吡啶基染料具有良好的生物相容性和低毒性,可应用于活细胞成像。

相似文献

1
Palladium-Catalyzed C-4 Selective Coupling of 2,4-Dichloropyridines and Synthesis of Pyridine-Based Dyes for Live-Cell Imaging.钯催化 2,4-二氯吡啶 C-4 选择性偶联及合成用于活细胞成像的吡啶基染料。
J Org Chem. 2020 May 15;85(10):6498-6508. doi: 10.1021/acs.joc.0c00449. Epub 2020 May 4.
2
Pyridine-NHC: effective ligand in Pd-catalyzed cyclopropanation of esters with substituted allyl carbonates.吡啶-N-杂环卡宾:钯催化酯与取代碳酸烯丙酯环丙烷化反应中的有效配体。
J Org Chem. 2014 Dec 19;79(24):12010-7. doi: 10.1021/jo5018712. Epub 2014 Oct 16.
3
Pd(II)-Catalyzed C3-Selective Arylation of Pyridine with (Hetero)arenes.钯(II)催化吡啶与(杂)芳烃的C3选择性芳基化反应
Org Lett. 2016 Feb 19;18(4):744-7. doi: 10.1021/acs.orglett.5b03712. Epub 2016 Feb 2.
4
Palladium-Catalyzed Cascade Reactions of δ-Ketonitriles with Arylboronic Acids: Synthesis of Pyridines.钯催化 δ-酮腈与芳基硼酸的串联反应:吡啶的合成。
ACS Comb Sci. 2020 Mar 9;22(3):114-119. doi: 10.1021/acscombsci.9b00198. Epub 2020 Feb 14.
5
Synthesis of naturally occurring pyridine alkaloids via palladium-catalyzed coupling/migration chemistry.通过钯催化的偶联/迁移化学合成天然存在的吡啶生物碱。
J Org Chem. 2003 Apr 18;68(8):3090-8. doi: 10.1021/jo026716p.
6
Direct oxidative arylation of aryl C - H bonds with aryl boronic acids via pd catalysis directed by the N,N-dimethylaminomethyl group.通过N,N-二甲基氨基甲基导向的钯催化实现芳基硼酸与芳基C-H键的直接氧化芳基化反应。
Chem Asian J. 2015 Apr;10(4):840-3. doi: 10.1002/asia.201403292. Epub 2015 Jan 21.
7
Synthesis of 3-(hetero)aryl tetrahydropyrazolo[3,4-c]pyridines by Suzuki-Miyaura cross-coupling methodology.通过铃木-宫浦交叉偶联方法合成3-(杂)芳基四氢吡唑并[3,4-c]吡啶
J Org Chem. 2014 Aug 15;79(16):7682-8. doi: 10.1021/jo5012015. Epub 2014 Jul 29.
8
Efficient synthesis of a GABA A alpha2,3-selective allosteric modulator via a sequential Pd-catalyzed cross-coupling approach.通过连续钯催化交叉偶联方法高效合成一种GABA A α2,3选择性变构调节剂。
J Org Chem. 2005 Jul 22;70(15):6034-9. doi: 10.1021/jo050741o.
9
Palladium-catalyzed regioselective benzylation-annulation of pyridine N-oxides with toluene derivatives via multiple C-H bond activations: benzylation versus arylation.钯催化的吡啶 N-氧化物与甲苯衍生物的区域选择性苄基化-环化:苄基化与芳基化。
Org Lett. 2015 Feb 6;17(3):414-7. doi: 10.1021/ol503238a. Epub 2015 Jan 21.
10
Three-component synthesis of perfluoroalkyl- or perfluoroaryl-substituted 4-hydroxypyridine derivatives and their palladium-catalyzed coupling reactions.全氟烷基或全氟芳基取代的 4-羟基吡啶衍生物的三组分合成及其钯催化偶联反应。
J Org Chem. 2010 Feb 5;75(3):726-32. doi: 10.1021/jo9022183.

引用本文的文献

1
Suzuki-Miyaura Coupling of Pinacolboronic Esters Catalyzed by a Well-Defined Palladium ‑Heterocyclic Carbene (NHC) Catalyst.由结构明确的钯-杂环卡宾(NHC)催化剂催化的频哪醇硼酸酯的铃木-宫浦偶联反应
ACS Med Chem Lett. 2025 Jun 3;16(6):1170-1174. doi: 10.1021/acsmedchemlett.5c00206. eCollection 2025 Jun 12.
2
Development of Subcritical Water Extraction for Areca Alkaloids and Its Influence on the Structure of Areca Nut Husk.槟榔碱亚临界水提取法的开发及其对槟榔壳结构的影响
Molecules. 2025 Feb 14;30(4):886. doi: 10.3390/molecules30040886.
3
Tuning the Chain Conformation of Pyrenyl-Pyridine Conjugated Oligomer Nanoprobe for Ultrasensitive Fluorescent Assaying of Fe and Ascorbic Acid.
用于铁和抗坏血酸超灵敏荧光检测的芘基吡啶共轭低聚物纳米探针链构象调控
J Fluoresc. 2025 Feb 13. doi: 10.1007/s10895-025-04158-5.
4
Discovery of intermolecular cascade annulation for dihydrobenzo[][1,8]naphthyridine-ylidene-pyrrolidinetriones.二氢苯并[][1,8]萘啶亚基-吡咯烷三酮分子间级联环化反应的发现
Chem Sci. 2025 Jan 28;16(9):4119-4126. doi: 10.1039/d4sc07999j. eCollection 2025 Feb 26.
5
Mechanistic Origin of Ligand Effects on Exhaustive Functionalization During Pd-Catalyzed Cross-Coupling of Dihaloarenes.二卤代芳烃钯催化交叉偶联反应中配体对彻底官能团化影响的机理起源
ACS Catal. 2024 May 3;14(9):7127-7135. doi: 10.1021/acscatal.4c00646. Epub 2024 Apr 23.
6
Nickel-Based Catalysts for the Selective Monoarylation of Dichloropyridines: Ligand Effects and Mechanistic Insights.用于二氯吡啶选择性单芳基化的镍基催化剂:配体效应及机理研究
ACS Catal. 2024 May 3;14(9):6404-6412. doi: 10.1021/acscatal.4c00648. Epub 2024 Apr 11.
7
Evidence for Suzuki-Miyaura cross-couplings catalyzed by ligated Pd-clusters: from cradle to grave.由连接的钯簇催化的铃木-宫浦交叉偶联反应的证据:从摇篮到坟墓。
Chem Sci. 2024 Jan 15;15(8):2763-2777. doi: 10.1039/d3sc06447f. eCollection 2024 Feb 22.
8
Different Oxidative Addition Mechanisms for 12- and 14-Electron Palladium(0) Explain Ligand-Controlled Divergent Site Selectivity.12电子和14电子钯(0)的不同氧化加成机制解释了配体控制的发散位点选择性。
ACS Catal. 2022 Aug 5;12(15):8822-8828. doi: 10.1021/acscatal.2c01698. Epub 2022 Jul 8.
9
Electrochemical study of 2-amino-5-mercapto-1,3,4-thiadiazole in the absence and presence of -benzoquinone: an efficient strategy for the electrosynthesis of new 1,3,4-thiadiazole derivatives.2-氨基-5-巯基-1,3,4-噻二唑在有无对苯醌存在下的电化学研究:一种电合成新型1,3,4-噻二唑衍生物的有效策略。
RSC Adv. 2023 Jan 19;13(5):3083-3094. doi: 10.1039/d2ra07250e. eCollection 2023 Jan 18.
10
The Road Less Traveled: Unconventional Site Selectivity in Palladium-Catalyzed Cross-Couplings of Dihalogenated -Heteroarenes.少有人走的路:钯催化二卤代杂芳烃交叉偶联反应中的非常规位点选择性
ACS Catal. 2022 Oct 7;12(19):12014-12026. doi: 10.1021/acscatal.2c03743. Epub 2022 Sep 19.