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Nickel‐catalyzed Nucleophilic C‐Borylation of Imines

Von Wiley-VCH zur Verfügung gestellt

The first Ni-catalyzed C -borylation of imine is disclosed. The addition of a boryl group gave the α-aminoboronate derivatives which were used for a peptide analog of bioactive compounds after treatment with Ac2O. A wide variety of aryl imines were tolerated under the developed conditions. The reaction of N-benzylimine was also accepted.


Application of bioisostere plays an important role in drug discovery. α-Aminoboronic acid is the familiar bioisostere of α-amino acid. Developing reactions for the synthesis of a wide variety of α-aminoboronic acid is one important task for synthetic chemistry. Herein, we report the development of nucleophilic C-borylation chemistry for N-arylimines catalyzed by nickel. The reaction proceeds through the insertion of a borylnickel species into the C=N bond to afford the corresponding α-aminoboronate, which was isolated as acetamide after trapping with acetic anhydride. N-Benzyl imine is also tolerated by the developed reaction.

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