Enantioselective C,P-Palladacycle-Catalyzed Arylation of Imines

Chiral diarylmethylamines are of great interest because of their prevalence in biological and pharmaceutical sciences. Herein, we report a C,P-palladacycle-catalyzed enantioselective synthesis of chiral diarylmethylamines via asymmetric arylation of N-protected imines with arylboronic acids. The C,P-palladacycle showed high reactivity (up to 99% yield) and enantioselectivity (up to 99% ee) toward this arylation, enabling the tolerance of a wide range of functionalities, providing a convenient and efficient access to enantiomerically enriched diarylmethylamines. The absolute configuration of the product was well rationalized by the proposed stereochemical pathway and the catalytical cycle.