Mild and efficient synthesis of secondary aromatic amines by one-pot stepwise reductive amination of arylaldehydes with nitroarenes promoted by reusable nickel nanoparticles

Abstract

The one-pot stepwise reductive amination of arylaldehydes with nitroarenes is described, using reusable nickel nanoparticles (Ni-pol) as catalyst and NaBH4 as mild, inexpensive, and safe reducing agent. The proposed catalytic system holds several advantages such as the use of a non-precious and earth-abundant metal, the facile separation of the catalyst from the reaction mixture by centrifugation, excellent stability towards air and moisture, very mild reaction conditions, good recyclability, broad substrate scope with good to excellent yields, and easy scalability (up to 1.0 g). FESEM analyses indicate that the active species are cubic nanocrystals of Ni in the average cross section value of 35 nm with a quite narrow (25–45 nm) and monomodal distribution, which becomes bimodal with the recycling reactions but without agglomeration.