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

Bibliographic Information

Published
2022-06-05
Resource Type
journal article
Rights Information
  • This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Macromolecules, copyright © 2022 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see Related DOI.
DOI
  • 10.1021/acs.orglett.2c01663
Publisher
American Chemical Society (ACS)

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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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