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.
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。
相似文献
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
Expanded ring diaminocarbene palladium complexes: synthesis, structure, and Suzuki-Miyaura cross-coupling of heteroaryl chlorides in water.扩展的环二氨基卡宾钯配合物：在水中的合成、结构和杂芳基氯的铃木-宫浦交叉偶联。
Dalton Trans. 2013 May 21;42(19):6859-66. doi: 10.1039/c3dt32860k.
3
N-Heterocyclic Carbene-Palladium Polymers Network: Recyclable Pre-catalyst for Effective Suzuki-Miyaura Coupling Reaction in Water.N-杂环卡宾-钯聚合物网络：可回收的水相Suzuki-Miyaura 偶联反应的预催化剂。
Chem Biodivers. 2023 Jun;20(6):e202201246. doi: 10.1002/cbdv.202201246. Epub 2023 May 30.
4
Highly efficient monophosphine-based catalyst for the palladium-catalyzed suzuki-miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters.用于钯催化杂芳基卤化物与杂芳基硼酸及酯的铃木-宫浦反应的高效单膦基催化剂。
J Am Chem Soc. 2007 Mar 21;129(11):3358-66. doi: 10.1021/ja068577p. Epub 2007 Feb 28.
5
Suzuki-Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene-palladium complex catalyst.聚合物负载的 N-杂环卡宾-钯配合物催化剂催化 1-芳基三氮唑与芳基硼酸的铃木-宫浦交叉偶联反应。
Beilstein J Org Chem. 2010 Jun 28;6:70. doi: 10.3762/bjoc.6.70.
6
A Bulky Chiral N-Heterocyclic Carbene Palladium Catalyst Enables Highly Enantioselective Suzuki-Miyaura Cross-Coupling Reactions for the Synthesis of Biaryl Atropisomers.一种庞大的手性 N-杂环卡宾钯催化剂实现了高对映选择性的铃木-宫浦交叉偶联反应，用于联芳基轴手性化合物的合成。
J Am Chem Soc. 2019 Sep 18;141(37):14938-14945. doi: 10.1021/jacs.9b08578. Epub 2019 Sep 6.
7
Phosphorus(III)-Compatible Asymmetric Suzuki-Miyaura Cross-Coupling (P-ASMC) Reaction.磷（III）兼容的不对称铃木-宫浦交叉偶联（P-ASMC）反应
J Am Chem Soc. 2025 Jun 18;147(24):20657-20666. doi: 10.1021/jacs.5c03816. Epub 2025 Jun 7.
8
Cross-coupling and dehalogenation reactions catalyzed by (N-heterocyclic carbene)Pd(allyl)Cl complexes.（N-杂环卡宾）钯（烯丙基）氯配合物催化的交叉偶联和脱卤反应
J Org Chem. 2004 Apr 30;69(9):3173-80. doi: 10.1021/jo035834p.
9
N-heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of aryl sulfonates with arylboronic acids.N-杂环卡宾-钯（II）-1-甲基咪唑配合物催化的芳基磺酸盐与芳基硼酸的Suzuki-Miyaura 偶联反应。
J Org Chem. 2012 Aug 3;77(15):6608-14. doi: 10.1021/jo301270t. Epub 2012 Jul 25.
10
Efficient catalyst for the Suzuki-Miyaura coupling of potassium aryl trifluoroborates with aryl chlorides.用于芳基三氟硼酸钾与芳基氯进行铃木-宫浦偶联反应的高效催化剂。
Org Lett. 2004 Aug 5;6(16):2649-52. doi: 10.1021/ol0491686.
本文引用的文献
1
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。
Chem Soc Rev. 2014 Jan 7;43(1):412-43. doi: 10.1039/c3cs60197h. Epub 2013 Oct 3.
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。
Angew Chem Int Ed Engl. 2013 Jul 15;52(29):7362-70. doi: 10.1002/anie.201301737. Epub 2013 Jun 18.
Zotero 插件