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Ring walking as a regioselectivity control element in Pd-catalyzed C-N cross-coupling

Author

Listed:
  • Madeleine C. Deem

    (University of British Columbia)

  • Joshua S. Derasp

    (University of British Columbia)

  • Thomas C. Malig

    (University of British Columbia)

  • Kea Legard

    (University of British Columbia)

  • Curtis P. Berlinguette

    (University of British Columbia
    The University of British Columbia
    The University of British Columbia
    MaRS Innovation Centre)

  • Jason E. Hein

    (University of British Columbia)

Abstract

Ring walking is an important mechanistic phenomenon leveraged in many catalytic C-C bond forming reactions. However, ring walking has been scarcely studied under Buchwald-Hartwig amination conditions despite the importance of such transformations. An in-depth mechanistic study of the Buchwald-Hartwig amination is presented focussing on ligand effects on ring walking behavior. The ability of palladium catalysts to promote or inhibit ring walking is strongly influenced by the chelating nature of the ligand. In stark contrast, the resting state of the catalyst had no impact on ring walking behavior. Furthermore, the complexity of the targeted system enabled the differentiation between catalysts which undergo ring walking versus diffusion-controlled coupling. The insights gained in this study were leveraged to achieve desymmetrization of a tetrabrominated precursor. A small library of asymmetric 2,2′,7,7′-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9’spirobifluorene (SpiroOMeTAD) derivatives were successfully synthesized using this strategy highlighting the ease with which libraries of these compounds can be accessed for screening.

Suggested Citation

  • Madeleine C. Deem & Joshua S. Derasp & Thomas C. Malig & Kea Legard & Curtis P. Berlinguette & Jason E. Hein, 2022. "Ring walking as a regioselectivity control element in Pd-catalyzed C-N cross-coupling," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30255-1
    DOI: 10.1038/s41467-022-30255-1
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    References listed on IDEAS

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    1. Michael Saliba & Simonetta Orlandi & Taisuke Matsui & Sadig Aghazada & Marco Cavazzini & Juan-Pablo Correa-Baena & Peng Gao & Rosario Scopelliti & Edoardo Mosconi & Klaus-Hermann Dahmen & Filippo De A, 2016. "A molecularly engineered hole-transporting material for efficient perovskite solar cells," Nature Energy, Nature, vol. 1(2), pages 1-7, February.
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    Cited by:

    1. Yao Shi & Joshua S. Derasp & Tristan Maschmeyer & Jason E. Hein, 2024. "Phase transfer catalysts shift the pathway to transmetalation in biphasic Suzuki-Miyaura cross-couplings," Nature Communications, Nature, vol. 15(1), pages 1-12, December.

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