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Updated: Dec 29, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Iron-Catalyzed Radical Cleavage/C-C Bond Formation of Acetal-Derived Alkylsilyl Peroxides
Yoko Shiozaki1, Shunya Sakurai1, Ryu Sakamoto1
1Department of Chemistry Graduate School of Science, Kyoto University Sakyo, Kyoto, 606-8502, Japan.
Abstract:
A novel radical-based approach for the iron-catalyzed selective cleavage of acetal-derived alkylsilyl peroxides, followed by the formation of a carbon-carbon bond is reported. The reaction proceeds under mild reaction conditions and exhibits a broad substrate scope with respect to the acetal moiety and the carbon electrophile. Mechanistic studies suggest that the present reaction proceeds through a free-radical process involving carbon radicals generated by the homolytic cleavage of a carbon-carbon bond within the acetal moiety. A synthetic application of this method to sugar-derived alkylsilyl peroxides is also described.
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