Photocatalyzed Formation of gem ‐Difluoroalkenes Using Oxime Esters - Institut Charles Gerhardt - Institut de Chimie Moléculaire et des Matériaux de Montpellier Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2024

Photocatalyzed Formation of gem ‐Difluoroalkenes Using Oxime Esters

Résumé

In this manuscript a general photocatalytic approach for the synthesis of alkyl‐substituted gem ‐difluoroalkenes using readily available oxime esters and 1‐bromo‐1,1‐difluoroprop‐2‐ene (BDFP) has been established. This strategy involving a radical bromo elimination provides access to a large variety of value‐added fluorinated molecules. The mild reaction conditions are compatible with many functional groups including complex natural products or drug molecules. Experimental and theoretical mechanistic investigations indicate that the efficiency of the process relies on the crucial role of imine radical, which is formed after photoexcitation via energy transfert (EnT) and decarboxylation of the oxime ester. Indeed, the imine radical would either behave as a bromine radical scavenger or an XAT promoter in this reaction.
Fichier principal
Vignette du fichier
Adv Synth Catal - 2024 - Geniller - Photocatalyzed Formation of gem‐Difluoroalkenes Using Oxime Esters.pdf (5.86 Mo) Télécharger le fichier
Origine Publication financée par une institution
licence

Dates et versions

hal-04571312 , version 1 (07-05-2024)

Licence

Identifiants

Citer

Lilian Geniller, Marc Taillefer, Eric Clot, Florian Jaroschik, Alexis Prieto. Photocatalyzed Formation of gem ‐Difluoroalkenes Using Oxime Esters. Advanced Synthesis and Catalysis, inPress, ⟨10.1002/adsc.202400174⟩. ⟨hal-04571312⟩
0 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Mastodon Facebook X LinkedIn More