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Stainless Steel-Mediated Hydrogen Generation from Alkanes and Diethyl Ether and Its Application for Arene Reduction

  • Yoshinari Sawama*
    Yoshinari Sawama
    Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
    *E-mail: [email protected] (Y. Sawama).
    More by Yoshinari Sawama
    Orcidhttp://orcid.org/0000-0002-9923-2412
  • , 
  • Naoki Yasukawa
    Naoki Yasukawa
    Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
    More by Naoki Yasukawa
  • , 
  • Kazuho Ban
    Kazuho Ban
    Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
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  • , 
  • Ryota Goto
    Ryota Goto
    Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
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  • , 
  • Miki Niikawa
    Miki Niikawa
    Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
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  • , 
  • Yasunari Monguchi
    Yasunari Monguchi
    Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
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    Orcidhttp://orcid.org/0000-0002-2141-3192
  • , 
  • Miki Itoh
    Miki Itoh
    Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
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  • , and 
  • Hironao Sajiki*
    Hironao Sajiki
    Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
    *E-mail: [email protected] (H. Sajiki).
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    Orcidhttp://orcid.org/0000-0003-2792-6826
Cite this: Org. Lett. 2018, 20, 10, 2892–2896
Publication Date (Web):May 1, 2018
https://doi.org/10.1021/acs.orglett.8b00931
Copyright © 2018 American Chemical Society
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    Abstract

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    Hydrogen gas can be generated from simple alkanes (e.g., n-pentane, n-hexane, etc.) and diethyl ether (Et2O) by mechanochemical energy using a planetary ball mill (SUS304, Fritsch Pulverisette 7), and the use of stainless steel balls and vessel is an important factor to generate the hydrogen. The reduction of organic compounds was also accomplished using the in-situ-generated hydrogen. While the use of pentane as the hydrogen source facilitated the reduction of the olefin moieties, the arene reduction could proceed using Et2O. Within the components (Fe, Cr, Ni, etc.) of the stainless steel, Cr was the metal factor for the hydrogen generation from the alkanes and Et2O, and Ni metal played the role of the hydrogenation catalyst.

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