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Anti-Markovnikov Hydroamination of Alkenes with Aqueous Ammonia by Metal-Loaded Titanium Oxide Photocatalyst

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    Anti-Markovnikov Hydroamination of Alkenes with Aqueous Ammonia by Metal-Loaded Titanium Oxide Photocatalyst
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    • Soyeong Park
      Soyeong Park
      Department of Interdisciplinary Environment, Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan
      More by Soyeong Park
    • Jaeyoung Jeong
      Jaeyoung Jeong
      Department of Interdisciplinary Environment, Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan
      More by Jaeyoung Jeong
    • Ken-ichi Fujita
      Ken-ichi Fujita
      Department of Interdisciplinary Environment, Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan
      More by Ken-ichi Fujita
      Orcidhttp://orcid.org/0000-0002-8362-2694
    • Akira Yamamoto
      Akira Yamamoto
      Department of Interdisciplinary Environment, Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan
      Elements Strategy Initiative for Catalysts and Batteries (ESICB), Kyoto University, Kyoto 606-8501, Japan
      More by Akira Yamamoto
      Orcidhttp://orcid.org/0000-0002-1329-0807
    • Hisao Yoshida*
      Hisao Yoshida
      Department of Interdisciplinary Environment, Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan
      Elements Strategy Initiative for Catalysts and Batteries (ESICB), Kyoto University, Kyoto 606-8501, Japan
      *[email protected]
      More by Hisao Yoshida
      Orcidhttp://orcid.org/0000-0002-2540-0225
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2020, 142, 29, 12708–12714
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    https://doi.org/10.1021/jacs.0c04598
    Published June 22, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    A completely new route was established to synthesize valuable primary amines from alkenes by using aqueous ammonia, that is, a simple photocatalytic hydroamination of alkenes using aqueous ammonia with a metal-loaded TiO2 photocatalyst. Although the photochemical hydroamination prefers to form amines according to the Markovnikov rule, the new photocatalytic hydroamination gives anti-Markovnikov products predominantly. With an Au-loaded TiO2 photocatalyst, the amine yield reached up to 93% and the regioselectivity of anti-Markovnikov products was above 98%. The reaction mechanism was proposed for the new photocatalytic hydroamination.

    Copyright © 2020 American Chemical Society

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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2020, 142, 29, 12708–12714
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.0c04598
    Published June 22, 2020
    Copyright © 2020 American Chemical Society
    Request reuse permissions

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