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A metal‐free, photoinduced aerobic tandem amine dehydrogenation/Povarov cyclization/aromatization reaction between  N ‐aryl glycine esters and indoles leads to tetracyclic 11 H ‐indolo[3,2‐ c ]quinolines under mild conditions and with high yields. The reaction can be performed by using molecular iodine along with visible light, or by combining an organic photoredox catalyst with a halide anion. Mechanistic studies reveal that product formation occurs through a combination of radical‐mediated oxidation steps with an iminium ion or N‐haloiminium ion [4+2]‐cycloaddition, and the N‐heterocyclic products constitute new analogues of the antiplasmodial natural alkaloid isocryptolepine.

Visible‐Light‐Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines