Copper Catalyzed Selective Monoarylation of Anilines by a New Reusable Catalyst Supported on Magnetic Mesoporous Silica

IF 2.3 4区化学 Q3 CHEMISTRY, PHYSICAL

Catalysis Letters Pub Date : 2025-09-17 DOI:10.1007/s10562-025-05173-8

Mahsa Sotoude, Yagoub Mansoori, Fatemeh Ghahramani, Abolfazl Bezaatpour

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Abstract

This study presents the anchoring of a Cu-complex onto a magnetite/SBA-15 composite material. The synthesis was achieved via sequential functionalization of magnetic mesoporous silica, first with (3-aminopropyl) triethoxysilane (APTES), followed by trichlorotriazine and tetraethylenepentamine (TEPA), resulting in the formation of Fe₃O₄@SBA-TEPA. Subsequent coordination of the grafted polyamine ligand with CuI in acetonitrile yielded the Cu-complex, Fe₃O₄@SBA-TEPA-Cu. Comprehensive characterization of the supported complex was performed using Fourier-transform infrared spectroscopy (FT-IR), and thermogravimetric analysis (TGA). The anchored Cu-catalyst displayed remarkable efficiency in catalyzing C-N bond formation via the Ullmann-type N-arylation of haloarenes and anilines under optimized reaction conditions, selectively producing the mono N-arylation product with high fidelity. The catalyst demonstrated outstanding recyclability, showing minimal deactivation over seven consecutive reaction cycles, highlighting its robustness and stability.

Graphical Abstract

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磁性介孔二氧化硅负载的铜催化苯胺选择性单芳基化反应

本研究将cu配合物锚定在磁铁矿/SBA-15复合材料上。通过磁性介孔二氧化硅的顺序功能化，首先与（3-氨基丙基）三乙氧基硅烷（APTES），然后与三氯三嗪和四乙基戊二胺（TEPA）进行功能化，形成Fe3O4@SBA-TEPA。接枝的多胺配体随后在乙腈中与CuI配位，得到cu配合物Fe3O4@SBA-TEPA-Cu。利用傅里叶变换红外光谱（FT-IR）和热重分析（TGA）对负载配合物进行了综合表征。在优化后的反应条件下，锚定cu催化剂催化卤代芳烃和苯胺的ullmann型n-芳基化反应形成C-N键，选择性地生成高保真的单n-芳基化产物。该催化剂表现出出色的可回收性，在连续七个反应周期中表现出最小的失活，突出了其鲁棒性和稳定性。图形抽象

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来源期刊

Catalysis Letters 化学-物理化学

CiteScore

5.70

自引率

3.60%

发文量

327

审稿时长

1 months

期刊介绍： Catalysis Letters aim is the rapid publication of outstanding and high-impact original research articles in catalysis. The scope of the journal covers a broad range of topics in all fields of both applied and theoretical catalysis, including heterogeneous, homogeneous and biocatalysis. The high-quality original research articles published in Catalysis Letters are subject to rigorous peer review. Accepted papers are published online first and subsequently in print issues. All contributions must include a graphical abstract. Manuscripts should be written in English and the responsibility lies with the authors to ensure that they are grammatically and linguistically correct. Authors for whom English is not the working language are encouraged to consider using a professional language-editing service before submitting their manuscripts.