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- Title
Photocatalyzed (3+2) Cycloaddition for the Dearomatization of Electron‐Poor Arenes under Flow Conditions.
- Authors
Faye, Youssou; Rkein, Batoul; Bigot, Antoine; Lequeux, Thierry; Legros, Julien; Chataigner, Isabelle
- Abstract
The photocatalyzed dearomative reaction between various electron‐deficient aromatic compounds and a non‐stabilized azomethine ylide is successfully performed in a flow system. Whereas the use of supported eosin as organic photocatalyst exhibits limited efficiency, turning to the soluble Rose Bengal allows to transform a broad range of substrates from hetarenes (indole, benzofuran, quinoline, pyridine) to naphthalenes and benzenes. This photocatalyzed (3+2) dearomative cycloaddition under green light irradiation provides a simple and efficient access to tridimensional pyrrolidino scaffolds with a tetrasubstituted carbon center at ring junction and can be performed in the friendly ethyl acetate. Computational studies support the mechanism involving azomethine ylide as reactive species toward the electron‐poor arene.
- Subjects
ELECTRON-deficient compounds; AROMATIC compounds; ROSE bengal; ETHYL acetate; SCHIFF bases; RING formation (Chemistry)
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 49, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202301567