Blue‐Light‐Induced Pd‐Catalyzed Quinolinamide‐Directed Regioselective C‐8 Benzylation of 1‐Naphthylamines Using Flow‐Generated Aryldiazomethanes in Batch and Continuous‐Flow

Herein, a continuous photo‐flow protocol for quinolinamide‐directed regioselective C‐8 benzylation of 1‐naphthylamine derivatives via CH bond functionalization with flow‐generated aryldiazomethanes is reported. A wide range of 8‐benzylated‐1‐naphthylamide products are afforded in satisfactory yields upon palladium catalysis via a bidentate directing process under illumination by 12 W blue light‐emitting diodes (450 nm). This mild, simple, and convenient synthetic method allows a wide range of easily handled aryl aldehydes, without the exclusion of either moisture or oxygen. This transformation is environmentally friendly and operationally simple, and it can be easily scaled up to the gram scale with good selectivity. Finally, an improved protocol for CH functionalization is described, which relies on the use of a continuous‐flow photo‐microreactor.