PDF herunterladen
Synthesis
DOI: 10.1055/a-2733-3887
Paper

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

Autoren

  • 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)

Gefördert durch: Japan Society for the Promotion of Science (JSPS) Grant number 23K04756
Weitere Informationen
 als PDF herunterladen Alle Artikel dieser Rubrik

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.



Publikationsverlauf

Eingereicht: 13. September 2025

Angenommen nach Revision: 27. Oktober 2025

Accepted Manuscript online:
27. Oktober 2025

© . Thieme. All rights reserved.

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany