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用于芳基卤化物和酰胺的铃木-宫浦交叉偶联反应的结构灵活的(噻唑-2-亚基)钯(烯丙基)氯配合物

Structurally Flexible (Thiazol-2-ylidene)Pd(Allyl)Cl Complexes for Suzuki-Miyaura Cross-Coupling of Aryl Halides and Amides.

作者信息

Wang Ruihong, Han Xiaoxia, Zhang Jin, Chen Nana, Sun Li, Zhang Gaopeng, Szostak Michal

机构信息

School of Food Science and Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China.

College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China.

出版信息

Org Lett. 2025 Sep 12;27(36):10054-10059. doi: 10.1021/acs.orglett.5c03118. Epub 2025 Sep 4.

Abstract

This study introduces a new class of (NHC)Pd(allyl)Cl complexes featuring thiazol-2-ylidene ligands, which exhibit enhanced steric and electronic properties compared to those of traditional imidazol-2-ylidenes. These air-stable Pd(II)-NHC catalysts demonstrate superior reactivity in chemoselective Suzuki-Miyaura cross-couplings of aryl bromides and amides. Kinetic studies reveal their superior reactivity over traditional imidazol-2-ylidene-based complexes. The findings highlight the potential of thiazole-based carbenes in advancing Pd-catalyzed cross-coupling reactions.

摘要

本研究介绍了一类新型的具有噻唑-2-亚基配体的(NHC)Pd(烯丙基)Cl配合物,与传统的咪唑-2-亚基相比,它们具有增强的空间和电子性质。这些空气稳定的Pd(II)-NHC催化剂在芳基溴化物和酰胺的化学选择性铃木-宫浦交叉偶联反应中表现出优异的反应活性。动力学研究表明,它们的反应活性优于传统的基于咪唑-2-亚基的配合物。这些发现突出了噻唑基卡宾在推进钯催化交叉偶联反应方面的潜力。

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本文引用的文献

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Site-Selective Copper--Heterocyclic Carbene-Catalyzed C(sp)-C(sp) Cross-Coupling of Aryl Thianthrenium Salts.
Org Lett. 2025 Apr 4;27(13):3440-3445. doi: 10.1021/acs.orglett.5c00875. Epub 2025 Mar 23.
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