Strain-promoted azide-alkyne cycloaddition enhanced by the secondary interactions

Azide-alkyne cycloaddition of cyclooct-2-yn-1-ol and 2-(azidophenyl)boronic acid proceeded rapidly at room temperature with complete regioselectivity to afford a triazole having a boronate ester group. The secondary covalent interaction of the boronate ester contributed to the rate acceleration and the control of regioselectivity. The interaction of an imine was also evaluated.