Photocatalytic Redox-Neutral Alkoxyacylation of Alkenes

β-Alkoxyketones are important building blocks in organic synthesis. By utilizing CBZ6, with an oxidative potential of −2.16 V (vs the saturated calomel electrode), as a redox-neutral photocatalyst, alkoxyacylation of olefins was accomplished under the irradiation of visible light via a cationic inte...

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Bibliographic Details
Published in:Organic letters 2023-12, Vol.25 (50), p.8997-9001
Main Authors: Cen, Fu-Tong, Sun, Yu, Qu, Jian-Ping, Kang, Yan-Biao
Format: Article
Language:English
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Summary:β-Alkoxyketones are important building blocks in organic synthesis. By utilizing CBZ6, with an oxidative potential of −2.16 V (vs the saturated calomel electrode), as a redox-neutral photocatalyst, alkoxyacylation of olefins was accomplished under the irradiation of visible light via a cationic intermediate. It involves the addition of an acyl radical to olefin to form a radical intermediate and the following oxidation of the radical intermediate to the benzyl cationic intermediate that is captured by alkoxy anions. This process provides concise and practical access to the β-functionalized ketones.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03583