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Updated: Jan 19, 2026

Light-driven Enzymatic Decarboxylation
Published on: May 22, 2016
Visible-Light-Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines
Eva Schendera1, Lisa-Natascha Unkel1, Phung Phan Huyen Quyen1
1Institute of Chemistry, Organic Chemistry, University of Rostock, Albert-Einstein-Strasse 3A, 18059, Rostock, Germany.
Abstract:
A metal-free, photoinduced aerobic tandem amine dehydrogenation/Povarov cyclization/aromatization reaction between N-aryl glycine esters and indoles leads to tetracyclic 11H-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.
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