Electrochemical amination. Selective introduction of two amino groups into an aromatic ring

Abstract

Indirect cathodic amination of anisole via a Ti(IV)–NH₂OH system in aqueous solutions of sulfuric acid is studied. The major products of the radical cation substitution in these media are para- and ortho-anisidines and 4-methoxy-1,3-phenylenediamine. The most efficient electrochemical process takes place in 10–12 М H₂SO₄. Under these conditions, complete conversion of the source of amino radicals is observed, and the total current yields, which correspond to the yields per hydroxylamine, reach 60%.