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Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling

Author

Listed:
  • Masakazu Nambo

    (Nagoya University)

  • Jacky C.-H. Yim

    (Nagoya University)

  • Luiza B. O. Freitas

    (Queen’s University)

  • Yasuyo Tahara

    (Nagoya University)

  • Zachary T. Ariki

    (Queen’s University)

  • Yuuki Maekawa

    (Queen’s University)

  • Daisuke Yokogawa

    (The University of Tokyo)

  • Cathleen M. Crudden

    (Nagoya University
    Queen’s University)

Abstract

α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting in improved biological activity and stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes are still rare. Herein we describe the Pd-catalyzed Suzuki-Miyaura cross-coupling of α-fluorinated benzylic triflones with arylboronic acids affording structurally diverse α-fluorinated diarylmethanes. The ease of synthesis of fluorinated triflones as the key starting materials enables powerful late-stage transformations of known biologically active compounds into fluorinated analogs.

Suggested Citation

  • Masakazu Nambo & Jacky C.-H. Yim & Luiza B. O. Freitas & Yasuyo Tahara & Zachary T. Ariki & Yuuki Maekawa & Daisuke Yokogawa & Cathleen M. Crudden, 2019. "Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-11758-w
    DOI: 10.1038/s41467-019-11758-w
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