Nucleophilic aromatic substitution of hydrogen: A novel electrochemical approach to the cyanation of nitroarenes

Research output: Contribution to journalArticleResearchpeer-review

41 Citations (Scopus)

Abstract

The nucleophilic aromatic substitution of hydrogen through electrochemical oxidation of the intermediate σ complexes (Meisenheimer complexes) in simple nitroaromatic compounds is reported for the first time. The studies have been carried out with hydride and cyanide anions as the nucleophiles using cyclic voltammetry (CV) and preparative electrolysis. The cyclic voltammetry experiments allow for the detection and characterization of the σ complexes and 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)1759-1765
JournalChemistry - A European Journal
Volume7
Issue number8
DOIs
Publication statusPublished - 17 Apr 2001

Keywords

  • σ complexes
  • Cyclic voltammetry
  • Electrochemistry
  • Meisenheimer complexes
  • Nucleophilic substitution

Fingerprint Dive into the research topics of 'Nucleophilic aromatic substitution of hydrogen: A novel electrochemical approach to the cyanation of nitroarenes'. Together they form a unique fingerprint.

Cite this