Nickel-catalyzed Nucleophilic C-Borylation of Imines

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.

Keywords: C-borylation; imines; nickel catalyst; α-aminoboronic ester.