Synthesis of 1-Vinyl/Arylbenzotriazole 3-Oxides through a Copper-Mediated C-N Bond Coupling Reaction

An efficient synthesis of 1-vinyl/arylbenzotriazole 3-oxides via the copper-promoted coupling of N-hydroxybenzotriazoles with alkenyl- or arylboronic acids is reported. This strategy features mild reaction conditions, good functional group tolerance, broad substrate scope and rapid introduction of benzotriazole N-oxide moieties into molecules. Density functional theory calculations revealed that the formation of the favored N-coupling product depends on the kinetically more favorable C-N bond formation pathway.