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Photocatalytic Addition Reactions of Ketene Silyl Acetals with Alkenes through Formation of α‐Carbonyl Radicals

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Photocatalytic addition reactions of ketene silyl acetals with alkenes bearing no electron-withdrawing group are reported. By using appropriate protic additives, the desired reactions proceeded smoothly to afford the desired products through formation of α-carbonyl radicals.


Abstract

Addition reactions of ketene silyl acetals with alkenes that do not have an electron-withdrawing group are generally difficult because the nucleophilicity of ketene silyl acetals and the electrophilicity of alkenes are not sufficient. Herein, we report photocatalytic addition reactions of ketene silyl acetals with alkenes that proceed through formation of α-carbonyl radicals. In the presence of an appropriate protic additive, the reactions proceeded smoothly under blue-light irradiation to afford the desired products in moderate to high yields.

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