Boronate Formation-Triggered Azide-Alkyne Cycloaddition

Abstract

A catalyst-free triazole formation reaction between o-borylaryl azides and N-propargyldiethanolamine derivatives is reported. Control experiments demonstrated that the triazole formation was triggered by boronate formation, which brought the azido group and alkyne moiety into close proximity. This boronate formation-triggered azide-alkyne cycloaddition (BAAC) reaction exhibited orthogonality to other azide-alkyne cycloaddition reactions, enabling sequential double-click conjugations with diazido or dialkyne compounds.