Nucleophilic aromatic substitution for heteroatoms: An oxidative electrochemical approach

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Abstract

The nucleophilic aromatic substitution for heteroatom through electrochemical oxidation of the intermediate σ-complexes (Meisenheimer complexes) in simple nitroaromatic compounds is reported for the first time (NASX process). The studies have been carried out with hydride, cyanide, fluoride, methoxy, and ethanethiolate anions and n-butylamine as a nucleophile, at the cyclic voltammetry (CV) and preparative electrolysis level. The cyclic voltammetry experiments allow for detection and characterization of the σ-complexes and they have led us to a proposal for the mechanism of the oxidation step. Furthermore, the power of the CV technique in the analysis of the reaction mixture throughout the whole chemical and electrochemical process is described.
Original languageEnglish
Pages (from-to)2548-2555
JournalJournal of Organic Chemistry
Volume67
Issue number8
DOIs
Publication statusPublished - 19 Apr 2002

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