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Ruthenium-Catalyzed Cross-Selective Asymmetric Oxidative Coupling of Arenols

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2020, 22, 4, 1469-1474
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    Ruthenium-Catalyzed Cross-Selective Asymmetric Oxidative Coupling of Arenols
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    • Hiroki Hayashi
      Hiroki Hayashi
      Faculty of Arts and Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan
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    • Takamasa Ueno
      Takamasa Ueno
      Department of Chemistry, Graduate School of Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan
      More by Takamasa Ueno
    • Chungsik Kim
      Chungsik Kim
      International Institute of Carbon-Neutral Energy Research (WPI-I2CNER), Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan
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    • Tatsuya Uchida*
      Tatsuya Uchida
      Faculty of Arts and Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan
      International Institute of Carbon-Neutral Energy Research (WPI-I2CNER), Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan
      *[email protected]
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      Orcidhttp://orcid.org/0000-0002-6511-5752
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    Organic Letters

    Cite this: Org. Lett. 2020, 22, 4, 1469–1474
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    https://doi.org/10.1021/acs.orglett.0c00048
    Published January 27, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    (Aqua)ruthenium(salen) complex 1c achieved good to high chemo- and enantioselective oxidative cross-coupling of arenols. The catalytic system can be used to selectively produce C1-symmetric bis(arenol)s from the combination of C3- and C7-substituted 2-naphthols or phenols even when there is no significant difference in oxidation potential between the cross-coupling partners. This unique cross-selectivity is dominated by steric rather than electronic effects of the arenols and can be controlled by chemoselective single-electron oxidation and oxidative carbon–carbon bond formation.

    Copyright © 2020 American Chemical Society

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    Supporting Information

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    • Optimization, oxidation potentials of arenols, experimental procedures, characterization data, computational data, HPLC conditions, and NMR spectra (PDF)

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    Organic Letters

    Cite this: Org. Lett. 2020, 22, 4, 1469–1474
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.0c00048
    Published January 27, 2020
    Copyright © 2020 American Chemical Society
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