Photocatalyzed (3+2) Cycloaddition for the Dearomatization of Electron‐Poor Arenes under Flow Conditions
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.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Photocatalyzed (3+2) Cycloaddition for the Dearomatization of Electron‐Poor Arenes under Flow Conditions ; day:27 ; month:07 ; year:2023 ; extent:7
Chemistry - a European journal ; (27.07.2023) (gesamt 7)
- Creator
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Faye, Youssou
Rkein, Batoul
Bigot, Antoine
Lequeux, Thierry
Legros, Julien
Chataigner, Isabelle
- DOI
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10.1002/chem.202301567
- URN
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urn:nbn:de:101:1-2023072815222736596525
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 11:04 AM CEST
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Associated
- Faye, Youssou
- Rkein, Batoul
- Bigot, Antoine
- Lequeux, Thierry
- Legros, Julien
- Chataigner, Isabelle
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Polyene and Arene (4+1) Cycloaddition at a Seven‐Membered Cyclic Alumanyl
The Electrochemical Iodination of Electron‐Deficient Arenes
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Photoschaltbare Resorc[4]arene : photochrome supramolekulare Wirtsysteme durch intramolekulare [4+4]-Cycloaddition von Anthracen
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Brønsted Acid Catalysis Permits Electrophilic Halogenation of Electron-Deficient Arenes
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