Hydrogenative amination of furfural with aromatic amines in the presence of palladium catalysts

Hydrogenative amination of furfural with aromatic amines under mild conditions (0.1 MPa, 20-60 °C, Pd/C or Pd-containing anion exchangers, organic solvents) was studied. The reaction was found to proceed via the formation of corresponding azomethines followed by their hydrogenation to give N-tetrahydrofurfuryl aromatic amines. The yield of the latter varies from 4 to 100% depending on the nature of the aminating agent. The reaction rate decreases linearly as the Hammett constant of the substituent in the aromatic ring of the aminating agent increases.