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One-Pot Photomediated Giese Reaction/Friedel–Crafts Hydroxyalkylation/Oxidative Aromatization To Access Naphthalene Derivatives from Toluenes and Enones

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    Research Article

    One-Pot Photomediated Giese Reaction/Friedel–Crafts Hydroxyalkylation/Oxidative Aromatization To Access Naphthalene Derivatives from Toluenes and Enones
    Click to copy article linkArticle link copied!

    • Haiwang Liu
      Haiwang Liu
      Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Republic of Singapore
      More by Haiwang Liu
    • Lishuang Ma
      Lishuang Ma
      College of Chemistry, Beijing Normal University, Beijing 100875, People’s Republic of China
      More by Lishuang Ma
    • Rong Zhou
      Rong Zhou
      Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Republic of Singapore
      College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024, People’s Republic of China
      More by Rong Zhou
    • Xuebo Chen*
      Xuebo Chen
      College of Chemistry, Beijing Normal University, Beijing 100875, People’s Republic of China
      *E-mail for X.C.: [email protected]
      More by Xuebo Chen
      Orcidhttp://orcid.org/0000-0002-9814-9908
    • Weihai Fang
      Weihai Fang
      College of Chemistry, Beijing Normal University, Beijing 100875, People’s Republic of China
      More by Weihai Fang
      Orcidhttp://orcid.org/0000-0002-1668-465X
    • Jie Wu*
      Jie Wu
      Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Republic of Singapore
      *E-mail for J.W.: [email protected]
      More by Jie Wu
      Orcidhttp://orcid.org/0000-0002-9865-180X
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    ACS Catalysis

    Cite this: ACS Catal. 2018, 8, 7, 6224–6229
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    https://doi.org/10.1021/acscatal.8b00481
    Published May 29, 2018
    Copyright © 2018 American Chemical Society
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    Abstract

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    Value-added chemicals, γ-aryl ketones and naphthalenes, were conveniently synthesized from readily available toluenes and enones through the synergistic combination of photoredox and Lewis acid catalysis. The direct synthesis of γ-aryl ketones represents a rare example of Giese reactions between benzylic C(sp3)–H and enones that avoids the use of prefunctionalized metallic nucleophiles. Naphthalene derivatives were accessed through a one-pot Giese reaction/Friedel–Crafts hydroxyalkylation/oxidative aromatization sequential transformation.

    Copyright © 2018 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acscatal.8b00481.

    • Detailed experimental procedures, characterization data, and 1H NMR and 13C NMR spectra of final products (PDF)

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    This article is cited by 55 publications.

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    ACS Catalysis

    Cite this: ACS Catal. 2018, 8, 7, 6224–6229
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acscatal.8b00481
    Published May 29, 2018
    Copyright © 2018 American Chemical Society
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