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Article Dans Une Revue Journal of Organic Chemistry Année : 2019

Photoinduced Non­–stabilized Azomethine Ylide Formation for the Preparation of Fluorine Containing Pyrrolidines

Résumé

A mild and reproducible method for the formation of a nonstabilized azomethine ylide was developed by photoinduced reaction catalyzed with eosin Y under green light irradiation. Resulting 1,3-dipole was trapped with fluoroalkenes, fluoroalkylated alkenes, and representative dipolarophiles to access pyrrolidine scaffolds, including spirocyclic compounds. The mechanism involved in this transformation was investigated, showing clearly a catalytic redox cycle with eosin Y.

Domaines

Chimie organique
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Dates et versions

hal-02127271 , version 1 (13-05-2019)

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Citer

Thierry Thibault, Cyril Lebargy, Emmanuel Pfund, Thierry Lequeux. Photoinduced Non­–stabilized Azomethine Ylide Formation for the Preparation of Fluorine Containing Pyrrolidines. Journal of Organic Chemistry, 2019, 84 (9), pp.5877-5885. ⟨10.1021/acs.joc.9b00244⟩. ⟨hal-02127271⟩
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