The synthetic potential of N-aminopyridinium salts as versatile nitrogen radical surrogates has been demonstrated in various transformations including cycloaddition and difunctionalization reactions of alkenes and alkynes. However, application of these salts for the reaction with BCBs may pose considerable challenges due to the highly reactive nature of BCBs, raising concerns about regio-and chemoselectivity issues, and therefore, leading to undesired reaction pathways.