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Chlorine-Substituted 9,10-Dihydro-9-aza-10-boraanthracene as a Precursor for Various Boron- and Nitrogen-Containing π-Conjugated Compounds
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    Chlorine-Substituted 9,10-Dihydro-9-aza-10-boraanthracene as a Precursor for Various Boron- and Nitrogen-Containing π-Conjugated Compounds
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    • Yutaro Ishikawa
      Yutaro Ishikawa
      Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan
    • Katsunori Suzuki*
      Katsunori Suzuki
      Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan
      *E-mail: [email protected]
    • Kohei Hayashi
      Kohei Hayashi
      Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan
    • Shin-ya Nema
      Shin-ya Nema
      Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan
      More by Shin-ya Nema
    • Makoto Yamashita*
      Makoto Yamashita
      Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan
      *E-mail: [email protected]
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    Organic Letters

    Cite this: Org. Lett. 2019, 21, 6, 1722–1725
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    https://doi.org/10.1021/acs.orglett.9b00278
    Published March 6, 2019
    Copyright © 2019 American Chemical Society

    Abstract

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    Chlorine-substituted 9,10-dihydro-9-aza-10-boraanthracene was synthesized. Derivatization of this compound by taking advantage of the transformable B–Cl moiety gave 9,10-dihydro-9-aza-10-boraanthracene derivatives with various aryl substituents. In addition, further functionalization on NH groups by alkylation and Buchwald–Hartwig amination was demonstrated. Photophysical properties of the resulting 9,10-dihydro-9-aza-10-boraanthracene derivatives were also discussed.

    Copyright © 2019 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.9b00278.

    • Details of experiments, X-ray crystallography, NMR and UV–vis spectra, and DFT calculations (PDF)

    • Cartesian coordination of optimized structures (XYZ)

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    CCDC 18924941892498 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Organic Letters

    Cite this: Org. Lett. 2019, 21, 6, 1722–1725
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.9b00278
    Published March 6, 2019
    Copyright © 2019 American Chemical Society

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