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本文引用的文献

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Prescribed drugs containing nitrogen heterocycles: an overview.含氮杂环的处方药:概述
RSC Adv. 2020 Dec 15;10(72):44247-44311. doi: 10.1039/d0ra09198g. eCollection 2020 Dec 9.
2
Imidazo[1,2-b]pyridazine as privileged scaffold in medicinal chemistry: An extensive review.咪唑并[1,2-b]哒嗪作为药物化学中的优势骨架:一篇广泛的综述。
Eur J Med Chem. 2021 Dec 15;226:113867. doi: 10.1016/j.ejmech.2021.113867. Epub 2021 Sep 23.
3
Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis.(杂)芳基硼酸酯的脱硼保护:直接途径与预水解途径和自/自催化。
J Am Chem Soc. 2021 Sep 15;143(36):14814-14826. doi: 10.1021/jacs.1c06863. Epub 2021 Aug 30.
4
Heteroaryl-Heteroaryl, Suzuki-Miyaura, Anhydrous Cross-Coupling Reactions Enabled by Trimethyl Borate.三甲基硼酸促进的杂芳基-杂芳基、铃木-宫浦、无水交叉偶联反应。
J Am Chem Soc. 2021 Sep 1;143(34):13845-13853. doi: 10.1021/jacs.1c06419. Epub 2021 Aug 20.
5
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.
6
Base-Catalyzed Aryl-B(OH) Protodeboronation Revisited: From Concerted Proton Transfer to Liberation of a Transient Aryl Anion.碱催化的芳基-B(OH)2 脱硼酸反应再研究:从协同质子转移到瞬态芳基阴离子的释放。
J Am Chem Soc. 2017 Sep 20;139(37):13156-13165. doi: 10.1021/jacs.7b07444. Epub 2017 Sep 11.
7
An insight on synthetic and medicinal aspects of pyrazolo[1,5-a]pyrimidine scaffold.吡唑并[1,5-a]嘧啶骨架的合成及药用方面的见解。
Eur J Med Chem. 2017 Jan 27;126:298-352. doi: 10.1016/j.ejmech.2016.11.019. Epub 2016 Nov 10.
8
Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals.分析美国 FDA 批准的药物中氮杂环的结构多样性、取代模式和频率。
J Med Chem. 2014 Dec 26;57(24):10257-74. doi: 10.1021/jm501100b. Epub 2014 Oct 7.
9
Selection of boron reagents for Suzuki-Miyaura coupling.用于 Suzuki-Miyaura 偶联反应的硼试剂的选择。
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10
Transmetalation in the Suzuki-Miyaura coupling: the fork in the trail.铃木-宫浦偶联中的转金属化反应:分岔的小径。
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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

Suzuki-Miyaura Coupling of Pinacolboronic Esters Catalyzed by a Well-Defined Palladium ‑Heterocyclic Carbene (NHC) Catalyst.

作者信息

Logvinov Aleksei A, Rombouts Geert, Jouffroy Matthieu, Nolan Steven P

机构信息

Department of Chemistry and Centre for Sustainable Chemistry, Ghent University, Campus Sterre, Krijgslaan 281-S3, 9000 Ghent, Belgium.

Global Discovery Chemistry, Janssen Pharmaceutica NV, a Johnson & Johnson Company, 2340 Beerse, Belgium.

出版信息

ACS Med Chem Lett. 2025 Jun 3;16(6):1170-1174. doi: 10.1021/acsmedchemlett.5c00206. eCollection 2025 Jun 12.

DOI:10.1021/acsmedchemlett.5c00206
PMID:40529066
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12169495/
Abstract

We report a versatile synthetic method for coupling heteroaryl chlorides and bromides with (hetero)-aryl pinacolboronic esters of pharmaceutical interest at low catalyst loading of a well-defined palladium-NHC catalyst providing products in good to high isolated yield and purity in short reaction time. The method displays remarkably broad applicability with both 5- and 6-membered heterocycles.

摘要

我们报道了一种通用的合成方法,该方法能在明确的钯-氮杂环卡宾催化剂低负载量的情况下,将杂芳基氯化物和溴化物与具有药物活性的(杂)芳基频哪醇硼酸酯进行偶联反应,在短反应时间内以良好至高的分离产率和纯度得到产物。该方法对五元环和六元环杂环均显示出显著广泛的适用性。