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Updated: Jul 20, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Nickel-catalyzed Nucleophilic C-Borylation of Imines
Hisayasu Ishibashi1, Soshi Nishino1, Koki Shibata1
1Department of Chemical Engineering, National Institute of Technology, Nara College, 22 Yata, Yamatokoriyama, Nara, Japan.
Abstract:
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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