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 NO group on the product.