Ligand‐Controlled Copper‐Catalyzed Regiodivergent Carbonylative Synthesis of α‐Amino Ketones and α‐Boryl Amides from Imines and Alkyl Iodides
Fu‐Peng Wu, Xiao‐Feng Wu
Abstract
Abstract 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 ‐CF 3 C 6 H 4 ) 3 P as the ligand, whereas the corresponding α‐boryl amides were obtained with high regioselectivities when using Me IMes as the ligand.
Topics & Concepts
RegioselectivityLigand (biochemistry)IMesChemistryAlkylCatalysisMedicinal chemistryCopperSelectivityCombinatorial chemistryOrganic chemistryStereochemistryCarbeneReceptorBiochemistryOrganoboron and organosilicon chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions