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Updated: Jan 10, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Reductive Coupling of Acrylamides and Carbonyls via Solvated Electrons from Excited State Acridyl Radicals
Roukaya K El Mokadem1,2, Tanya M Lazarus1,2, David A Nicewicz1,3
1Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States.
Abstract:
The reductive coupling of carbonyls and alkenes is primarily promoted by super stoichiometric quantities of samarium diiodide (SmI2). This reductant requires fresh preparation under moisture-free anaerobic conditions for successful reactivity. Herein, we describe a new method for reductive coupling of acrylamides with unactivated ketones and aldehydes by employing acridine radicals as excited state reductants. Ultrafast transient absorption spectroscopy experiments provided a clearer picture of the excited state acridine radical and its mechanism of action, which likely proceeds via the formation of solvated electrons in acetonitrile.
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