Ligand-Controlled Copper-Catalyzed Regiodivergent Carbonylative Synthesis of α-Amino Ketones and α-Boryl Amides from Imines and Alkyl Iodides.

Regioselective transformation is among the long-standing challenges in organic synthesis. In this communication, a copper-catalyzed selectivity controlled regiodivergent borocarbonylation of imines with alkyl iodides has been developed. Various α-amino ketones and α-boryl amides were produced in moderate to good yields from the same substrates. The choice of the ligand is key for the regioselectivity control: α-amino ketones were produced selectively in good yields with (p-CF3 C6 H4 )3 P as the ligand, whereas the corresponding α-boryl amides were obtained with high regioselectivities when using Me IMes as the ligand.