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 the reaction that synthesize wide variety of α‐aminoboronic acid is one of the important task for synthetic chemistry. Herein, we report the development of nucleophilic C‐borylation chemistry for N‐arylimines catalyzed by Ni. The reaction proceeds through the insertion of a borylnickel species into the C=N bond to afford the corresponding α‐aminoboronate, which were isolated as acetamide after trapping with acetic anhydride. N‐Tosyl and benzyl imine is also tolerated by the developed reaction.