Department of Chemistry Graduate School of Science, Kyoto University Sakyo, Kyoto, 606-8502, Japan.
Graduate School of Pharmaceutical Sciences, Kyoto University Sakyo, Kyoto, 606-8501, Japan.
Chem Asian J. 2020 Mar 2;15(5):573-576. doi: 10.1002/asia.201901695. Epub 2020 Feb 11.
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.
本文报道了一种新型的基于自由基的方法，用于铁催化选择性断裂缩醛衍生的烷基硅基过氧化物，随后形成碳-碳键。该反应在温和的反应条件下进行，并具有广泛的底物范围，涉及缩醛部分和碳亲电试剂。机理研究表明，本反应通过自由基过程进行，涉及缩醛部分碳-碳键的均裂产生的碳自由基。该方法在糖衍生的烷基硅基过氧化物中的合成应用也有所描述。
