Visible-light-induced transition metal and photosensitizer free decarbonylative addition of amino-arylaldehydes to ketones |
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| Authors: | Yi Wang Yatao Lang Chao-Jun Li Huiying Zeng |
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| Institution: | The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Road, Lanzhou 730000 P. R. China.; Department of Chemistry, FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke St. West, Montreal, Quebec H3A 0B8 Canada |
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| 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.A visible-light-induced, transition-metal and external photosensitizer free decarbonylative addition of benzaldehydes to ketones/aldehydes via anion intermediates at room temperature is developed. |
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