Arylative Cyclization of 2-Isocyanobiphenyls with Anilines: One-Pot Synthesis of 6-Arylphenanthridines via Competitive Reaction Pathways

A transition-metal-free method for the synthesis of C6 phenanthridine derivatives by arylative cyclization of 2-isocyanobiphenyls with arylamines in one pot was developed. Mechanistic studies suggest that electrophilic aromatic substitution (SEAr) of a nitrilium intermediate and homolytic aromatic substitution (HAS) of an imidoyl radical intermediate are two competitive reaction pathways involved in the annulation step.