Electrogenerated acetonitrile anion induced selective N-alkylation of bifunctional compounds

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• 作者：Marta Feroci^a ; ^{marta.feroci@uniroma1.it} ; Daniela De Vita^b ; Luigi Scipione^b ; Giovanni Sotgiu^c ; Silvano Tortorella^b
• 关键词：Acetonitrile anion ; Electrosynthesis ; Alkylation ; Cycloserine ; 1 ; 2-Amino alcohols
• 刊名：Tetrahedron Letters
• 出版年：2012
• 出版时间：16 May, 2012
• 年：2012
• 卷：53
• 期：20
• 页码：2564-2567
• 全文大小：3429 K

文摘

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, ¦Â-amino alcohols, 2-substituted anilines) obtaining high yields. m>Nm>,m>Nm>-bis-alkylation has never been observed, indicating that the electrochemical methodology is highly regioselective.