Photocatalyzed (3+2) Cycloaddition for the Dearomatization of Electron‐Poor Arenes under Flow Conditions - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2023

Photocatalyzed (3+2) Cycloaddition for the Dearomatization of Electron‐Poor Arenes under Flow Conditions

Youssou Faye
  • Fonction : Auteur
Batoul Rkein
  • Fonction : Auteur
Antoine Bigot
  • Fonction : Auteur
Thierry Lequeux

Résumé

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.

Domaines

Chimie
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Dates et versions

hal-04250204 , version 1 (20-10-2023)

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Youssou Faye, Batoul Rkein, Antoine Bigot, Thierry Lequeux, Julien Legros, et al.. Photocatalyzed (3+2) Cycloaddition for the Dearomatization of Electron‐Poor Arenes under Flow Conditions. Chemistry - A European Journal, 2023, 29 (49), pp.45-52. ⟨10.1002/chem.202301567⟩. ⟨hal-04250204⟩
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