Rh(I)-Catalyzed Coupling of Azides with Boronic Acids Under Neutral Conditions.

ABSTRACT

Because of the importance of polyfunctional amines, C-N bond formation is important in synthetic organic chemistry. Here we present a neutral amination reaction using azides as the nitrogen source and arylboronic acids with a rhodium(I) catalyst to afford alkyl-aryl and aryl-aryl secondary amines. Natural products and pharmaceutical derivatives were applied, and gram-scale reactions were performed, which demonstrated the utility. Mechanistic experiments and DFT calculations suggested that the reaction involves a metal-nitrene intermediate.