Base- and Visible-Light-Promoted Formation of 3-Benzyl-3-Methoxyisoindolin-1-one

Martin, Nathan; Moncomble, Aurélien; Pelinski, Lydie; Deniau, Eric; Bousquet, Till

Document type :

Article dans une revue scientifique: Article original

DOI :

10.1002/ejoc.202400025

Permalink :

http://hdl.handle.net/20.500.12210/115139

Title :

Base- and Visible-Light-Promoted Formation of 3-Benzyl-3-Methoxyisoindolin-1-one

Author(s) :

Martin, Nathan [Auteur]
Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181
Moncomble, Aurélien [Auteur]

Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement (LASIRE) - UMR 8516
Pelinski, Lydie [Auteur]

Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181
Deniau, Eric [Auteur]

Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181
Bousquet, Till [Auteur]

Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181

Journal title :

Eur. J. Org. Chem.

Abbreviated title :

Eur. J. Org. Chem.

Volume number :

Pages :

Publication date :

2024-06-08

ISSN :

1434-193X

English keyword(s) :

photochemistry
diazonium salts
3-benzyl-3-methoxyisoindolin-1-ones

HAL domain(s) :

Chimie/Chimie théorique et/ou physique
Chimie/Catalyse

English abstract : [en]

Aryl diazonium salts are versatile compounds known for their reactivity in various transformations. In this study, we explored the arylation of 3-methylene isoindolinones using aryl diazonium salts. The objective was to ...
Show more >Aryl diazonium salts are versatile compounds known for their reactivity in various transformations. In this study, we explored the arylation of 3-methylene isoindolinones using aryl diazonium salts. The objective was to develop a method for accessing 3-benzyl-3-methoxyisoindolin-1-ones, a class of compounds with diverse biological activities and synthetic importance. Optimization of the reaction conditions revealed the significance of light irradiation for improved yields. The substrate scope investigation demonstrated the compatibility of various diazonium salts and N-substituents on the 3-methylene isoindolinone scaffold, yielding the corresponding methoxy lactams with high yields. Mechanistic insights were obtained by observing the effect of base and light irradiation. Two initiation mechanisms were proposed: in the presence of a base, the reaction could proceed even without light irradiation, while light irradiation was necessary in the absence of a base. DFT calculations were performed to elucidate the mechanism of the reaction and provide energetic considerationsShow less >

Language :

Anglais

Audience :

Internationale

Popular science :

Non

Administrative institution(s) :

Université de Lille
CNRS

Collections :

Research team(s) :

Physicochimie de l’Environnement (PCE)
Catalyse et synthèse éco-compatible (CASECO)

Submission date :

2024-06-13T21:02:49Z
2024-06-26T06:48:27Z

Files

Eur J Org Chem - 2024 - Martin - Base‐ and Visible‐Light‐Promoted Formation of 3‐Benzyl‐3‐Methoxyisoindolin‐1‐one.pdf
Version éditeur
Open access
Access the document

Except where otherwise noted, this item's license is described as Attribution-NonCommercial-NoDerivs 3.0 United States

Version	Link	Modification date
2	20.500.12210/115139*	2024-06-26T06:41:02Z
1	20.500.12210/115139.1	2024-06-13T21:02:49Z

Base- and Visible-Light-Promoted Formation ...

BibTeX

CSV

Excel

RIS

Files

Version history

Base- and Visible-Light-Promoted Formation ... BibTeX CSV Excel RIS

Files

Version history

Base- and Visible-Light-Promoted Formation ...

BibTeX

CSV

Excel

RIS