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Photocyclization of diarylethylenes with a boronate moiety: a useful synthetic tool to soluble PAH building blocksf

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Abstract

The synthesis of ten ortho-fused PAHs bearing boronic pinacol ester groups (BPin) is reported. The products are obtained via modification of Mallory photocyclization in 45–99% yields. Among them are examples of highly strained molecules such as [4]helicene derivatives with BPin substituents in the cavity. The method allows double C–C coupling and tolerates more than one BPin functionality.

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Authors and Affiliations

  1. Friedrich-Alexander University Erlangen-Nuernberg, Department of Chemistry and Pharmacy, Organic Chemistry II, Nikolaus-Fiebiger Str. 10, 91058, Erlangen, Germany

    Mikhail Feofanov, Arber Uka & Konstantin Amsharov

  2. Institute of Chemistry, Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Kurt-Mothes-Strasse 2, D-06120, Halle, Germany

    Mikhail Feofanov, Vladimir Akhmetova & Konstantin Amsharov

  3. South Ural State University, pr. Lenina 76, 454080, Chelyabinsk, Russia

    Konstantin Amsharov

Authors
  1. Mikhail Feofanov
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  2. Arber Uka
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  3. Vladimir Akhmetova
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  4. Konstantin Amsharov
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Correspondence to Konstantin Amsharov.

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Electronic supplementary information (ESI) available. See DOI: 10.1039/c9pp00497a

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Feofanov, M., Uka, A., Akhmetova, V. et al. Photocyclization of diarylethylenes with a boronate moiety: a useful synthetic tool to soluble PAH building blocksf. Photochem Photobiol Sci 19, 722–725 (2020). https://doi.org/10.1039/c9pp00497a

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  • DOI: https://doi.org/10.1039/c9pp00497a

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