Zn@CS: An Efficient Cu-Free Catalyst System for Direct Azide-Alkyne Cycloadditions and Multicomponent Synthesis of 4-Aryl-NH-1,2,3-triazoles in H2O and DES

A highly efficient recoverable and reusable heterogeneous Zn-catalyst, chitosan supported ZnSO 4 . 7H 2 O (designated as Zn@CS) is synthesized via a simple synthetic route. Low catalyst loading, need of aqueous reaction media and sharp reduction of time requirement in comparison to the previously re...

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Bibliographic Details
Published inCatalysis letters Vol. 153; no. 11; pp. 3516 - 3526
Main Authors Sultana, Jasmin, Garg, Anirban, Kulshrestha, Akshay, Rohman, Shahnaz S., Dutta, Bidyutjyoti, Singh, Kuldeep, Kumar, Arvind, Guha, Ankur K., Sarma, Diganta
Format Journal Article
LanguageEnglish
Published New York Springer US 01.11.2023
Springer Nature
Springer Nature B.V
Subjects
Alkynes
Aromatic compounds
Benzaldehyde
Biological activity
Catalysis
Catalysts
Chemistry
Chemistry and Materials Science
Chemistry, Physical
Chitosan
Copper
Cycloaddition
Industrial Chemistry/Chemical Engineering
Ligands
Nanoparticles
Nitrogen
Organometallic Chemistry
Pharmaceuticals
Physical Chemistry
Physical Sciences
Polymers
Science & Technology
Triazoles
ZnAAC
Biopolymeric support
Heterogeneous
DES
NH-1,2,3-triazoles
SODIUM-AZIDE
ONE-POT SYNTHESIS
CLICK CHEMISTRY
CHITOSAN
LIGATION
TERMINAL ALKYNES
ALDEHYDES
TRIAZOLES
NITROALKANES
CONDENSATION
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Summary:A highly efficient recoverable and reusable heterogeneous Zn-catalyst, chitosan supported ZnSO 4 . 7H 2 O (designated as Zn@CS) is synthesized via a simple synthetic route. Low catalyst loading, need of aqueous reaction media and sharp reduction of time requirement in comparison to the previously reported methodologies are some special features of the established Zn catalyzed direct azide-alkyne cycloaddition reaction. Zn@CS-catalyst is also suitable for multicomponent synthesis of 4-aryl-NH-1,2,3-triazoles from different derivatives of benzaldehyde. An inexpensive and environmentally benign deep eutectic solvent (DES), ChCl:PEG-400:Glycerol as a suitable reaction media accelerates these reactions leading to excellent yields of NH-triazoles. Based on literature report a plausible mechanism has been suggested for ZnAAC reaction. Graphical Abstract
ISSN:1011-372X
1572-879X
DOI:10.1007/s10562-022-04248-0