Building a Cocrystal by Using Supramolecular Synthons for Pressure-Accelerated Heteromolecular Azide-Alkyne Cycloaddition

Abstract

Facilitated by the supramolecular synthons of carboxylic acids and amides through cooperative hydrogen-bonding and arene-perfluoroarene interactions, the azide-alkyne cycloaddition reaction between two different molecules in a cocrystal was achieved. This reaction could be accelerated by pressure using a common hydraulic press equipment with excellent regioselectivity to yield 1,4-triazole products. The absence of decarboxylation side reactions in the products in the solid state demonstrated that this strategy can provide a green synthetic route for products not directly accessible by traditional syntheses in solution.

Keywords: arene-perfluoroarene interactions; crystal engineering; cycloaddition; high-pressure chemistry; supramolecular chemistry.