Synthesis of C2-symmetric and unsymmetrically substituted 2,2′-dipyridylamines and crystal structure of a chiral 2,2′-dipyridylamine copper(II) complex

C2-symmetric and unsymmetrically substituted 2,2′-dipyridylamines have been synthesized by sequential Buchwald–Hartwig aminations of halo-pyridines. The X-ray crystal structure of a copper dichloride complex bearing a C2-symmetric 2,2′-dipyridylamine reveals details of the binding properties of the ligand and the coordination geometry at the metal center. In preliminary experiments the use of the new nitrogen chelates in asymmetric catalysis has been demonstrated.