Nickel-NHC-catalyzed α-arylation of acyclic ketones and amination of haloarenes and unexpected preferential N-arylation of 4-aminopropiophenone

Article abstract of DOI:10.1021/jo070313d

(Chemical Equation Presented) Arylation of both acyclic ketones and primary and secondary amines was achieved using a new, simple, stable, and easy-to-access nickel(II)-halide complex bearing mixed PPh₃/N- heterocyclic carbene ligands as a catalyst precursor. Acyclic ketones were first arylated at the α-position with the nickel catalyst. On the other hand, less basic amines, such as diphenylamine and 4-aminobenzophenone, were more favorable in the catalytic amination of haloarenes than basic amines, contrary to previous reports. N-Arylation of 4-aminopropiophenone was found to proceed selectively without causing α-arylation of the ketone group.