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Direct ketone synthesis from primary alcohols and alkenes enabled by a dual photo/cobalt catalysis

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  • Guanghao Ji

    (Wuhan University)

  • Xinqiang Chen

    (Wuhan University)

  • Jing Zhang

    (Wuhan University)

Abstract

Catalytic methods to couple alcohol and alkene feedstocks are highly valuable in synthetic chemistry. The direct oxidative coupling of primary alcohols and alkenes offers a streamlined approach to ketone synthesis. Currently, available methods are based on transition metal-catalyzed alkene hydroacylation, which involves the generation of an electrophilic aldehyde intermediate from primary alcohol dehydrogenation. These methods generally require high reaction temperatures and a high loading of precious metal catalysts and are predominantly effective for branch-selective reactions with electron-rich alkenes. Herein, we designed a dual photo/cobalt-catalytic method to manipulate the reactivity of nucleophilic ketyl radicals for the synthesis of ketones from primary alcohols and alkenes in complementary reactivity and selectivity. This protocol exhibits exceptional scope across both primary alcohols and alkenes with high chemo- and regio-selectivity under mild reaction conditions. Mechanism investigations reveal the essential role of cobalt catalysis in enabling efficient catalysis and broad substrate scope.

Suggested Citation

  • Guanghao Ji & Xinqiang Chen & Jing Zhang, 2024. "Direct ketone synthesis from primary alcohols and alkenes enabled by a dual photo/cobalt catalysis," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-51190-3
    DOI: 10.1038/s41467-024-51190-3
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    References listed on IDEAS

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    1. Hui Cao & Yulong Kuang & Xiangcheng Shi & Koi Lin Wong & Boon Beng Tan & Jeric Mun Chung Kwan & Xiaogang Liu & Jie Wu, 2020. "Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    2. Julian G. West & David Huang & Erik J. Sorensen, 2015. "Acceptorless dehydrogenation of small molecules through cooperative base metal catalysis," Nature Communications, Nature, vol. 6(1), pages 1-7, December.
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