Photocatalyst-free visible-light triggered amination of benzo[c][1,2,5]thiadiazole: direct C–N bond formation from C(sp2)–H bond

Abstract

The photoredox amination of arene protocols mostly comprises photocatalyst-mediated transformations. Herein, we presented the photocatalyst-free, visible-light promoted, direct conversion of C(sp²)–H to C(sp²)–N method. Multipurpose benzothiadiazoles are used as model synthons and secondary amines as aminating agents. Mechanistic study reveals that the radical reaction mechanism proceeds through nitrogen-centered radical generation, followed by the addition of arenes, which was demonstrated for the present amination protocol of benzothiadiazole with secondary amines in an atom economical fashion.