Photocatalysis in Aqueous Micellar Media Enables Divergent C–H Arylation and N-Dealkylation of Benzamides

National Science Centre, Poland (SONATA 2018/31/D/ST5/00306).

Photocatalysis in aqueous micellar media has recently opened wide avenues to activate strong carbon−halide bonds. So far, however, it has mainly explored strongly reducing conditions, restricting the available chemical space to radical or anionic reactivity. Here, we demonstrate a controllable, photo catalytic strategy that channels the reaction of chlorinated benzamides via either a radical or a cationic pathway, enabling a chemodivergent C−H arylation or N-dealkylation. The catalytic system operates under mild conditions with methylene blue as a photocatalyst and blue LEDs as the light source. Factors determining the reactivity of substrates, their selectivity, and preliminary mechanistic studies are presented.