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

A mild and reproducible method for the formation of a non–stabilized 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.