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, beta-amino alcohols, 2-substituted anilines) obtaining high yields. N,N-bis-alkylation has never been observed, indicating that the electrochemical methodology is highly regioselective.
Electrogenerated acetonitrile anion induced selective N-alkylation of bifunctional compounds / Feroci, Marta; DE VITA, Daniela; Scipione, Luigi; Sotgiu, Giovanni; Tortorella, Silvano. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 53:20(2012), pp. 2564-2567. [10.1016/j.tetlet.2012.03.038]
Electrogenerated acetonitrile anion induced selective N-alkylation of bifunctional compounds
FEROCI, Marta;DE VITA, DANIELA;SCIPIONE, Luigi;TORTORELLA, Silvano
2012
Abstract
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, beta-amino alcohols, 2-substituted anilines) obtaining high yields. N,N-bis-alkylation has never been observed, indicating that the electrochemical methodology is highly regioselective.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
