Access to Biaryls via Anilide C–N Bond Activation through Photocatalytic Radical Truce–Smiles Rearrangement

C(aryl)-N bond activation of widely available anilines under mild conditions remains underdeveloped owing to the inert nature of anilines. Herein, Truce-Smiles rearrangement is employed to address this challenge by using naphthocarbazole as an organo-photoreductant, via a single-electron transfer process from readily accessible aryl chlorides and bromides tethered to anilines. This method offers a wide range of synthetically challenging 2-amidobiaryls, including sterically demanding ones. DFT calculations and control experiments were performed to elucidate the underlying reaction pathway.