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一种负载在勃姆石纳米颗粒上的新型席夫碱2-苯甲酰基吡啶基铜配合物,作为用于5-取代四唑的均相选择性合成的可回收纳米催化剂。

A new Schiff base 2-benzoylpyridine-based copper complex on boehmite nanoparticles as a recoverable nanocatalyst for the homoselective synthesis of 5-substituted tetrazoles.

作者信息

Mohseni Elham, Ghorbani-Choghamarani Arash, Tahmasbi Bahman, Norouzi Masoomeh

机构信息

Department of Chemistry, Faculty of Science, Ilam University P. O. Box 69315516 Ilam Iran

Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University Hamedan 6517838683 Iran

出版信息

RSC Adv. 2024 May 20;14(23):16269-16277. doi: 10.1039/d4ra03139c. eCollection 2024 May 15.

Abstract

In this study, boehmite nanoparticles (B-NPs) were prepared by a simple process and then their surface was modified by (3-aminopropyl)triethoxysilane (3-APTES). The modified B-NPs (3-APTES@B-NPs) were functionalized by 2-benzoylpyridine Schiff-base ligand toward the immobilization of the Schiff-base 2-benzoylpyridine ligand on the 3-APTES@B-NPs's surface (2BP-Schiff-base@B-NPs). Finally, copper ions were coordinated with the supported Schiff-base ligand on B-NPs toward the formation of the final catalyst (Cu-2BP-Schiff-base@B-NPs). The prepared Cu-2BP-Schiff-base@B-NPs were characterized using FT-IR spectroscopy, BET analysis, XRD, SEM, AAS, TGA, EDX and elemental mapping. Further, Cu-2BP-Schiff-base@B-NPs were applied as a homoselective and recyclable catalyst for the synthesis of a diverse range of 5-substituted tetrazoles in PEG-400 as a green solvent. The main benefits of this protocol are high homoselectivity attributes, short reaction times, high product yields and TOF values, and further addition to the catalyst ability to be recycled at least four times without significantly losing catalytic efficiency.

摘要

在本研究中,通过简单的工艺制备了勃姆石纳米颗粒(B-NPs),然后用(3-氨丙基)三乙氧基硅烷(3-APTES)对其表面进行改性。改性后的B-NPs(3-APTES@B-NPs)通过2-苯甲酰基吡啶席夫碱配体进行功能化,使席夫碱2-苯甲酰基吡啶配体固定在3-APTES@B-NPs的表面(2BP-席夫碱@B-NPs)。最后,铜离子与负载在B-NPs上的席夫碱配体配位,形成最终催化剂(Cu-2BP-席夫碱@B-NPs)。使用傅里叶变换红外光谱、BET分析、X射线衍射、扫描电子显微镜、原子吸收光谱、热重分析、能量散射X射线光谱和元素映射对制备的Cu-2BP-席夫碱@B-NPs进行了表征。此外,Cu-2BP-席夫碱@B-NPs作为一种均相选择性和可回收催化剂,用于在绿色溶剂聚乙二醇-400中合成多种5-取代四唑。该方法的主要优点是具有高均相选择性、反应时间短、产物收率和TOF值高,并且催化剂能够至少循环使用四次而不会显著降低催化效率。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d170/11103565/fcd88fc0ac72/d4ra03139c-s1.jpg

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