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Synthesis
DOI: 10.1055/a-2733-3887
Paper

Reductive Deoxygenation of Ketones with Silanes Catalyzed by Proton-Exchanged Montmorillonite to Olefin or Methylene Compounds

Authors

  • Yoshiki Tanaka

    1   Department of Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, Tokyo, Japan (Ringgold ID: RIN13126)

  • Shintaro Shibata 

    2   Research, Research Foundation Itsuu Laboratory, Kawasaki, Japan (Ringgold ID: RIN201216)

  • Takumi Yamamoto

    3   Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, Tokyo, Japan (Ringgold ID: RIN13126)

  • Yunosuke Ozawa

    3   Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, Tokyo, Japan (Ringgold ID: RIN13126)

  • Rei Miyazawa

    3   Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, Tokyo, Japan (Ringgold ID: RIN13126)

  • Momoka Koizumi

    4   日本, Tokyo University of Agriculture, Tokyo, Japan (Ringgold ID: RIN13126)

  • Akira Ishikawa

    3   Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, Tokyo, Japan (Ringgold ID: RIN13126)

  • Kimiko Hashimoto

    5   Department of Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture - Setagaya Campus, Tokyo, Japan (Ringgold ID: RIN13126)

  • Makoto Onaka

    3   Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, Tokyo, Japan (Ringgold ID: RIN13126)

Supported by: Japan Society for the Promotion of Science (JSPS) Grant number 23K04756
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We develop a novel process for the reductive deoxygenation of ketones using silanes, which affords olefin or methylene products. The reaction is catalyzed by proton-exchanged montmorillonite, a solid acid catalyst. Notably, cyclic or linear aliphatic ketones with carbonyl groups flanked by two primary carbon atoms selectively yield olefins. 1,2-Dibromides can also be produced directly from the ketones by adding bromine, without isolating the olefin intermediates. Therefore, 1,2-dibromides can be easily synthesized, even via volatile olefins that are difficult to handle. Meanwhile, aliphatic ketones bordered by secondary alkyl groups, diaryl ketones, cyclic benzoyl ketones, and aryl methyl ketones yield only methylene compounds.



Publication History

Received: 13 September 2025

Accepted after revision: 27 October 2025

Accepted Manuscript online:
27 October 2025

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