Photoinduced Divergent Deaminative Borylation and Hydrodeamination of Primary Aromatic Amines

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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
Pages (from-to)4281-4285
Number of pages5
JournalOrganic letters
Volume24
Issue number23
DOIs
Publication statusPublished - Jun 17 2022

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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