Iron-Catalyzed Radical Cleavage/C-C Bond Formation of Acetal-Derived Alkylsilyl Peroxides.

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.