2022Chemistry - An Asian JournalRequires access

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

Tsubasa Hirata, Yoshihiro Ogasawara, Shū Kobayashi, Yasuhiro Yamashita

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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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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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Available 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.

Key concepts: Ketene, Silylation, Chemistry, Electrophile, Radical, Nucleophile, Photochemistry, Acetal

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