Iron- and copper-based bifunctional catalysts for the base- and solvent-free C–N coupling of amines and aryl/benzyl chlorides under aerobic conditions

Abstract

The iron chalcogenide carbonyl cluster Fe₃Se₂(CO)₉ and Cu(OAc)₂ were found to be outstanding bimetallic catalysts for the C–N coupling reaction of amines and aryl chlorides. The reaction proceeds under base- and solvent-free conditions at 100 °C to produce excellent transformations of N-arylated products in just 4 h. The method works equally well for all the possible variants of amines, including aliphatic, aromatic and benzylic amine. The present C–N coupling method is highly economical, strongly feasible, and shows excellent competence with electron-withdrawing and base-sensitive functionalities. Moreover, it is the first report in which a zero-valent iron complex has been explored for C–N coupling reaction.