Fine Tuning of Quantum Dots Photocatalysts for the Synthesis of Tropane Alkaloid Skeletons - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2023

Fine Tuning of Quantum Dots Photocatalysts for the Synthesis of Tropane Alkaloid Skeletons

Ali Dabbous
Eloïse Colson
  • Fonction : Auteur
Debargha Chakravorty
Jean‐marie Mouesca
Christian Lombard
  • Fonction : Auteur
Sylvain Caillat
  • Fonction : Auteur
Fabien Dubois
  • Fonction : Auteur
Fabrice Dénès
  • Fonction : Auteur
Philippe Renaud

Résumé

Abstract Several types of Quantum Dots (QDs) (CdS, CdSe and InP, as well as core‐shell QDs such as type I InP‐ZnS, quasi type‐II CdSe‐CdS and inverted type‐I CdS‐CdSe) were considered for generating α‐aminoalkyl free radicals. The feasibility of the oxidation of the N ‐aryl amines and the generation of the desired radical was evidenced experimentally by quenching of the photoluminescence of the QDs and by testing a vinylation reaction using an alkenylsulfone radical trap. The QDs were tested in a radical [3+3]‐annulation reaction giving access to tropane skeletons and that requires the completion of two consecutive catalytic cycles. Several QDs such as CdS core, CdSe core and inverted type I CdS‐CdSe core‐shell proved to be efficient photocatalysts for this reaction. Interestingly, the addition of a second shorter chain ligand to the QDs appeared to be essential to complete the second catalytic cycle and to obtain the desired bicyclic tropane derivatives. Finally, the scope of the [3+3]‐annulation reaction was explored for the best performing QDs and isolated yields that compare well with classical iridium photocatalysis were obtained.

Domaines

Chimie
Fichier principal
Vignette du fichier
manuscript_chem202300303R1.pdf (2.15 Mo) Télécharger le fichier
supporting information_chem202300303R1.pdf (10.55 Mo) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)
Origine : Publication financée par une institution

Dates et versions

hal-04393441 , version 1 (14-01-2024)

Identifiants

Citer

Ali Dabbous, Eloïse Colson, Debargha Chakravorty, Jean‐marie Mouesca, Christian Lombard, et al.. Fine Tuning of Quantum Dots Photocatalysts for the Synthesis of Tropane Alkaloid Skeletons. Chemistry - A European Journal, 2023, 29 (28), ⟨10.1002/chem.202300303⟩. ⟨hal-04393441⟩
5 Consultations
10 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More