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

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

doi:10.1016/j.ijbiomac.2022.04.075

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

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

Authors

Mohaddeseh Sajjadi¹, Mahmoud Nasrollahzadeh², Hossein Ghafuri¹, Talat Baran³, Yasin Orooji⁴, Nuray Yılmaz Baran⁵, Mohammadreza Shokouhimehr⁶

Affiliations

¹ Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran.
² Department of Chemistry, Faculty of Science, University of Qom, PO Box 37185-359, Qom, Iran. Electronic address: m.nasrollahzadeh@qom.ac.ir.
³ Department of Chemistry, Faculty of Science and Letters, Aksaray University, 68100 Aksaray, Turkey.
⁴ College of Geography and Environmental Sciences, Zhejiang Normal University, Jinhua 321004, China; Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Materials Science and Engineering, Nanjing Forestry University, Nanjing, 210037, PR China.
⁵ Technical Vocational School, Department of Chemistry Technology, Aksaray University, 68100 Aksaray, Turkey.
⁶ Department of Materials Science and Engineering, Research Institute of Advanced Materials, Seoul National University, Seoul 08826, Republic of Korea.

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

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 K₄[Fe(CN)₆] as a non-toxic cyanide source to catalyze the [2 + 3] cycloaddition of the corresponding aryl nitriles with NaN₃ 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.

Keywords: 5-Substituted-1H-tetrazoles; Aryl nitriles; Biopolymer-supported Pd complex; Chitosan; Cyanation; Cycloaddition.

MeSH terms

Catalysis
Chitosan*
Inorganic Chemicals*
Nanoparticles*
Palladium
Tetrazoles
Zeolites*

Substances

Inorganic Chemicals
Tetrazoles
Zeolites
1H-tetrazole
Palladium
Chitosan