Visible-Light-Induced C-N Bond Formation

Perylene derivatives Py (5 mM), PdTPBP (25 μM), K₂CO₃ (3 equiv.), inert aryl bromide/chloride (1 equiv.) and a magnetic stir bar were added to a dried 5 mL borosilicate vial. After purging the vial with argon, solvent (2 mL) and heteroarene (2 equiv.) were added by syringe. To complete the oxygen-remove for reaction mixture, three cycles of vacuum evacuation at −78 °C and then argon fill when returning to room temperature, was operated on the sealed vial. Subsequently, the reaction vial was irradiated by a 656 nm LED placed approximately 2 cm far, with slow stirring (400 rpm). After a few hours, the reaction was quenched with water (10 mL) and extracted with DCM (×2), and then the combined organic layers were dried over MgSO₄. The crude material was then purified by column chromatography on silica gel using the mixture solvents of dichloromethane (DCM) and n-hexane (1/1, v/v) as elution solution to furnish the desired product.