Organocatalytic-assisted synthesis of 1,2,3-triazoles mediated by chitosan beads

Abstract

In this study, we explore the potential of chitosan beads as an organocatalyst for the synthesis of 1,2,3-triazoles. The chitosan beads were prepared using a straightforward coagulation process, yielding beads with a narrow size distribution (2.34 ± 0.21 mm), significant porosity, and high stability under proposed experimental conditions. Under optimized conditions, the chitosan beads (20 mg) exhibited efficient catalytic activity, assisting the synthesis of diverse 1,4,5-trisubstituted-1,2,3-triazoles with yields ranging from 27 % to 97 %. The protocol proved compatible with 1,3-diketones, β-keto-esters, and α-cyano-ketones, while azides bearing electron-withdrawing groups demonstrate enhanced efficiency compared to electron-donating counterparts. Importantly, the bead-like structure of chitosan was shown to be crucial in achieving high yields of 1,2,3-triazoles. This study introduces chitosan as a green and versatile organocatalyst for synthesizing valuable organic compounds like triazoles, offering new insights into its application in sustainable chemistry.