Sonochemistry- and mechanochemistry-driven one-pot synthesis of polyfunctionalised 5-iodo-1H-1,2,3-triazoles through a copper(I)-catalysed click chemistry

Abstract

We herein report a dual synthetic approach that integrates sono- and mechanochemical strategies to access a diverse array of 5-iodo-1H-1,2,3-triazoles through a copper(I)-catalysed click reaction of aryl/heteroaryl acetylenes with benzyl bromides, sodium azide, and copper iodide (CuI). CuI acts herein for the first time as both a catalyst and an iodine source. Both synthetic protocols provide a straightforward, efficient, and practical platform for accessing this important class of biologically and synthetically valuable organic compounds. The salient features of the newly developed methods include mild reaction conditions, avoidance of external heating and oxidants, shorter reaction times (in minutes), good to excellent yields with high regioselectivity, broad substrate scope and tolerance of other various functional groups, low E-factors, gram-scale synthetic applicability, and reusability of the solid surface (mechanochemical). Besides, a few selected synthesised 5-iodo-triazoles were converted into a range of biorelevant molecular scaffolds, as part of the synthetic application.