Issue 35, 2020

Photoinduced iodine-mediated tandem dehydrogenative Povarov cyclisation/C–H oxygenation reactions

Abstract

We report metal-free, photoinduced aerobic tandem dehydrogenative Povarov cyclisation/Csp3–H oxygenation reactions between N-aryl glycine esters and α-substituted styrenes, which efficiently lead to 4,4-disubstituted dihydroquinoline-3-ones under mild conditions. The reactions are mediated by iodine along with visible light irradiation, which allows for the in situ generation of the essential Brønsted acid HI, to catalyse the key imine [4+2]-cycloaddition.

Graphical abstract: Photoinduced iodine-mediated tandem dehydrogenative Povarov cyclisation/C–H oxygenation reactions

Supplementary files

Article information

Article type
Paper
Submitted
20 Jul 2020
Accepted
14 Aug 2020
First published
24 Aug 2020

Org. Biomol. Chem., 2020,18, 6912-6915

Photoinduced iodine-mediated tandem dehydrogenative Povarov cyclisation/C–H oxygenation reactions

E. Schendera, A. Villinger and M. Brasholz, Org. Biomol. Chem., 2020, 18, 6912 DOI: 10.1039/D0OB01494J

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