Stoichiometric Reductive C-N Bond Formation of Arylgold(III) Complexes with N-Nucleophiles

The reductive formation of substituted anilines from amines and three well-defined arylgold(III) complexes, i.e., dichloro(2,6-lutidine)phenylgold(III) (2), dichloro(2,6-lutidine)-p-tolylgold(III) (3), and chlorobis(triphenylphosphine) phenylgold(III) chloride (4) was studied. The reaction is stoichiometric in gold and represents a key step of a potential gold-catalyzed intermolecular amination reaction of arenes. It proceeds smoothly with a broad range of N-nucleophiles in the presence of sodium acetate (NaOAc) and enables the selective formation of N-substituted anilines in good yields. A mechanistic pathway is proposed and discussed as well.