Electrogenerated acetonitrile anion induced selective N-alkylation of bifunctional compounds

The simple galvanostatic reduction of a solution of MeCN-0.1 M Et4NPF6 leads to the formation of acetonitrile anion, whose counter-ion is the Et4N+ cation, which leaves the anion ‘naked’. This enhances the reactivity of acetonitrile anion, which reveals to be selective in the N-monoalkylation of bifunctional compounds (cycloserine, β-amino alcohols, 2-substituted anilines) obtaining high yields. N,N-bis-alkylation has never been observed, indicating that the electrochemical methodology is highly regioselective.