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改性壳聚糖-沸石负载钯纳米粒子:一种用于由芳基卤化物合成5-取代-1H-四唑的可重复使用催化剂。

Modified chitosan-zeolite supported Pd nanoparticles: A reusable catalyst for the synthesis of 5-substituted-1H-tetrazoles from aryl halides.

作者信息

Sajjadi Mohaddeseh, Nasrollahzadeh Mahmoud, Ghafuri Hossein, Baran Talat, Orooji Yasin, Baran Nuray Yılmaz, Shokouhimehr Mohammadreza

机构信息

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

Department of Chemistry, Faculty of Science, University of Qom, PO Box 37185-359, Qom, Iran.

出版信息

Int J Biol Macromol. 2022 Jun 1;209(Pt A):1573-1585. doi: 10.1016/j.ijbiomac.2022.04.075. Epub 2022 Apr 18.

DOI:10.1016/j.ijbiomac.2022.04.075
PMID:35447267
Abstract

A novel heterogeneous catalyst has been developed using chitosan-zeolite supported Pd nanoparticles (PdNPs@CS-Zeo) and used in an efficient synthesis of 5-substituted-1H-tetrazoles from aryl halides with high yields for relatively short reaction times with an easy work-up procedure. In this method, highly effective and reusable PdNPs@CS-Zeo catalyst was used in the reaction of various aryl iodides/bromides with K[Fe(CN)] as a non-toxic cyanide source to catalyze the [2 + 3] cycloaddition of the corresponding aryl nitriles with NaN in the sequential one-pot preparation of 5-substituted-1H-tetrazoles. The synthesized PdNPs@CS-Zeo nanocatalyst was characterized using XRD, FTIR, TEM, HRTEM, XPS, Raman, TG-DTG, ICP-OES, BET, and EDS mapping. Additionally, the nanocatalyst could be effectively separated by filtration and reused for multiple times without significant decrease of catalytic activity.

摘要

一种新型多相催化剂已通过壳聚糖-沸石负载钯纳米颗粒(PdNPs@CS-Zeo)制备而成,并用于由芳基卤化物高效合成5-取代-1H-四唑,反应时间相对较短,产率高,后处理程序简便。在该方法中,高效且可重复使用的PdNPs@CS-Zeo催化剂用于各种芳基碘化物/溴化物与K[Fe(CN)](作为无毒氰化物源)的反应,以催化相应芳基腈与NaN在连续一锅法制备5-取代-1H-四唑过程中的[2 + 3]环加成反应。使用XRD、FTIR、TEM、HRTEM、XPS、拉曼光谱、TG-DTG、ICP-OES、BET和EDS映射对合成的PdNPs@CS-Zeo纳米催化剂进行了表征。此外,该纳米催化剂可通过过滤有效分离,并多次重复使用,而催化活性无明显降低。

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