Photoinduced Divergent Deaminative Borylation and Hydrodeamination of Primary Aromatic Amines

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  • Shiozuka, Akira
    Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
  • Sekine, Kohei
    Institute for Materials Chemistry and Engineering, Kyushu University Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
  • Toki, Takumi
    Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
  • Kawashima, Kyohei
    Institute for Materials Chemistry and Engineering, Kyushu University
  • Mori, Toshifumi
    Institute for Materials Chemistry and Engineering, Kyushu University Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
  • Kuninobu, Yoichiro
    Institute for Materials Chemistry and Engineering, Kyushu University Interdisciplinary Graduate School of Engineering Sciences, Kyushu University

Description

We have developed the divergent deaminative borylation and hydrodeamination of primary aromatic amines using bis(pinacolato)diboron. These transformations can be switched by the reaction conditions. Mechanistic and computational studies have suggested that the cleavage of the C–N bond and the formation of C–B bond are unlikely to involve free aryl radical intermediates. However, hydrodeamination is shown to proceed via hydrogen atom transfer between the corresponding aryl radical and an ethereal solvent.

Journal

  • Organic Letters

    Organic Letters 24 (23), 4281-4285, 2022-06-05

    American Chemical Society (ACS)

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