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Issue 23, 2018
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Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs)

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Abstract

We report the facile formation of trifluoroborate-iminiums (TIMs) from potassium acyltrifluoroborates (KATs) and the transformation of TIMs to α-aminotrifluoroborates by reduction or Grignard additions. Conditions for the hydrolysis of α-aminotrifluoroborates to α-aminoboronic acids, which are important biologically active compounds, were established. This new methodology allows access to sterically demanding α-aminoboronic acids that are not easily prepared with currently available methods. This work also introduces TIMs, that can be easily prepared and handled, as a new category of functional groups that serve as precursors to valuable organic compounds.

Graphical abstract: Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs)

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Publication details

The article was received on 01 Apr 2018, accepted on 12 May 2018 and first published on 16 May 2018


Article type: Edge Article
DOI: 10.1039/C8SC01486H
Citation: Chem. Sci., 2018,9, 5191-5196
  • Open access: Creative Commons BY-NC license
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    Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs)

    T. Shiro, A. Schuhmacher, M. K. Jackl and J. W. Bode, Chem. Sci., 2018, 9, 5191
    DOI: 10.1039/C8SC01486H

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