Strain-promoted azide–alkyne cycloaddition enhanced by secondary interactions

Abstract

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 interaction to form a boronate ion contributed to cycloaddition rate acceleration and the control of regioselectivity. The interaction to form an imine or hemiaminal was also evaluated.