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

Org Biomol Chem

University of Rostock, Institute of Chemistry, Albert-Einstein-Str. 3A, 18055 Rostock, Germany.

Published: September 2020

AI Article Synopsis

  • The study introduces a metal-free method for a photoinduced tandem reaction that synthesizes 4,4-disubstituted dihydroquinoline-3-ones from N-aryl glycine esters and α-substituted styrenes.
  • The process utilizes iodine and visible light to create a necessary Brønsted acid, HI, which acts as a catalyst.
  • This approach operates under mild conditions, making it a potentially more efficient and environmentally friendly alternative to traditional methods.

Article Abstract

We report metal-free, photoinduced aerobic tandem dehydrogenative Povarov cyclisation/C-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.

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Source
http://dx.doi.org/10.1039/d0ob01494jDOI Listing

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