Photoinduced Divergent Deaminative Borylation and Hydrodeamination of Primary Aromatic Amines

Akira Shiozuka, Kohei Sekine, Takumi Toki, Kyohei Kawashima, Toshifumi Mori, Yoichiro Kuninobu

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
JournalOrganic letters
DOIs
Publication statusAccepted/In press - 2022

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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