Biosourced cyclosophoraose-driven acceleration of click reaction in H2O

Abstract

Here, we report biosourced cyclosophoraose (CyS)-promoted click reaction of organic azides and alkynes in water, where CyS, rhizobial cyclic β-1,2 glucan molecules containing 17–23 glucoses, dramatically decreased the reaction time from hours to minutes via the solubilization of aromatic alkynes. This catalytic system was successfully applied to the copper-mediated Huisgen 1,3-dipolar cycloaddition reaction using in situ-generated azide. The developed strategy yielded 1,4-disubstituted-1,2,3-triazoles after a short reaction time without bases from a room-temperature aqueous medium, and the products were purified simply by precipitation without requiring further column purifications.