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Updated: Jan 16, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Organophotoredox Dioxygenation of Alkenes via ROH···F-Activated N-Alkoxyphthalimides
Pau Sarró1, Albert Gallego-Gamo1, Elies Molins2
1Department of Chemistry and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universitat Autònoma de Barcelona, Cerdanyola del Vallès, 08193 Barcelona, Spain.
Abstract:
The generation and controlled reactivity of alkoxyl radicals remain challenging due to their high energy and tendency for β-scission or hydrogen atom transfer events. Herein, we report a photoredox-catalyzed dioxygenation of alkenes enabled by the activation of fluorinated N-alkoxyphthalimides through hydrogen-bonded aggregates with ROH···F. This transformation proceeds under mild, metal-free conditions using an organophotocatalyst and a simple alcohol, affording a diverse range of dialkoxylated products with high functional group tolerance and good scalability. Mechanistic studies─including UV-Vis spectroscopy, NMR, cyclic voltammetry, and Stern-Volmer quenching─reveal a radical/polar crossover pathway.
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