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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

  • 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
  • , and 
  • 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]
Cite this: Org. Lett. 2019, 21, 6, 1722–1725
Publication Date (Web):March 6, 2019
https://doi.org/10.1021/acs.orglett.9b00278
Copyright © 2019 American Chemical Society

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    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.

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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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    Cited By

    This article is cited by 14 publications.

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