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铜(II)-β-环糊精固载在石墨相氮化碳纳米片上作为一种高效的催化剂用于苄醇的串联氧化氨化反应。

Copper(II)-β-cyclodextrin immobilized on graphitic carbon nitride nanosheets as a highly effective catalyst for tandem oxidative amidation of benzylic alcohols.

机构信息

Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, 16846-13114, Tehran, Iran.

出版信息

Sci Rep. 2022 Feb 11;12(1):2331. doi: 10.1038/s41598-022-05363-z.

Abstract

In this study, an efficient catalyst based on graphitic carbon nitride nanosheets (CN) and copper(II) supported β-cyclodextrin (β-CD/Cu(II)) was synthesized and used for tandem oxidative amidation of benzylic alcohols. In this regard, CN was functionalized by β-CD/Cu(II) via 1,3-dibromopropane linker (CN-Pr-β-CD/Cu(II)). The prepared catalyst was characterized using FT-IR, XRD, FE-SEM, EDS, TGA, ICP-OES, BET, and TEM analyses. CN-Pr-β-CD/Cu(II) was subsequently applied in a direct oxidative amidation reaction and it was observed that different benzyl alcohols were converted to desire amides with good to excellent efficiency. This reaction was performed in the presence of amine hydrochloride salts, tert-butyl hydroperoxide (TBHP), and CaCO in acetonitrile (CHCN) under nitrogen atmosphere. CN-Pr-β-CD/Cu(II) can be recycled and reused five times without significant reduction in reaction efficiency.

摘要

在这项研究中,合成了一种基于石墨相氮化碳纳米片(CN)和负载铜(II)的β-环糊精(β-CD/Cu(II))的高效催化剂,并将其用于苄醇的串联氧化酰胺化反应。在这方面,通过 1,3-二溴丙烷连接剂(CN-Pr-β-CD/Cu(II))使 CN 官能化。使用 FT-IR、XRD、FE-SEM、EDS、TGA、ICP-OES、BET 和 TEM 分析对制备的催化剂进行了表征。随后,将 CN-Pr-β-CD/Cu(II)用于直接氧化酰胺化反应,观察到不同的苄醇转化为所需酰胺,收率良好至优秀。该反应在氮气气氛下,在盐酸盐、叔丁基过氧化氢(TBHP)和碳酸钙存在下,于乙腈(CHCN)中进行。CN-Pr-β-CD/Cu(II)可回收并重复使用五次,而反应效率没有明显降低。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e3a/8837611/0e9232b0c48d/41598_2022_5363_Fig1_HTML.jpg

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