Mechanochemical Access to Functional Clickates with Nitro-Retentive Selectivity via Organocatalyzed Oxidative Azide-Olefin Cycloaddition

4-Nitro-1,2,3-triazoles
are crucial precursors for high energy
materials, and their practical synthesis is a long-standing problem.
Herein, we communicate a mechanochemical route for the selective synthesis
of 4-nitro-1,2,3-triazoles via organocatalyzed oxidative [3 + 2] cycloaddition
between β-nitrostyrenes and organic azides. Our conditions avoid
divergent pathways and permit the retention of the valuable NO2 group on the product. Nontoxic catalyst, catalyst recyclability,
no rigorous solvent-extraction, no toxic byproducts, atmospheric oxygen,
and gram-scale synthesis are some of the salient features.