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Visible-light-induced transition metal and photosensitizer free decarbonylative addition of amino-arylaldehydes to ketones.

ABSTRACT: The decarbonylative-coupling reaction is generally promoted by transition metals (via organometallic complexes) or peroxides (via radical intermediates), often at high temperatures to facilitate the CO release. Herein, a visible-light-induced, transition metal and external photosensitizer free decarbonylative addition of benzaldehydes to ketones/aldehydes at room temperature is reported. Tertiary/secondary alcohols were obtained in moderate to excellent yields promoted by using CsF under mild conditions. The detailed mechanistic investigation showed that the reaction proceeded through photoexcitation-decarbonylation of the aldehyde to generate an aromatic anion, followed by its addition to ketones/aldehydes. The reaction mechanism was verified by the density functional theory (DFT) calculations.

SUBMITTER: Wang Y

PROVIDER: S-EPMC8768876 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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Visible-light-induced transition metal and photosensitizer free decarbonylative addition of amino-arylaldehydes to ketones.

Wang Yi Y Lang Yatao Y Li Chao-Jun CJ Zeng Huiying H

Chemical science 20211221 3

The decarbonylative-coupling reaction is generally promoted by transition metals (<i>via</i> organometallic complexes) or peroxides (<i>via</i> radical intermediates), often at high temperatures to facilitate the CO release. Herein, a visible-light-induced, transition metal and external photosensitizer free decarbonylative addition of benzaldehydes to ketones/aldehydes at room temperature is reported. Tertiary/secondary alcohols were obtained in moderate to excellent yields promoted by using CsF ...[more]

PMID: 35173934

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