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. 2019 May 3;84(9):5877-5885.
doi: 10.1021/acs.joc.9b00244. Epub 2019 Apr 19.

Photoinduced Nonstabilized Azomethine Ylide Formation for the Preparation of Fluorine Containing Pyrrolidines

Thibault Thierry  1 , Cyril Lebargy  1 , Emmanuel Pfund  1 , Thierry Lequeux  1
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Photoinduced Nonstabilized Azomethine Ylide Formation for the Preparation of Fluorine Containing Pyrrolidines

Thibault Thierry et al. J Org Chem. .

Abstract

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.

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