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Gallardo I, Guirado G, Marquet J. Cathodically activated nucleophilic aromatic substitution of hydrogen: a novel electrochemical mechanism. Chem Commun (Camb). 2002;(22):2638-9doi: 10.1039/b207168a.
Gallardo, I., Guirado, G., & Marquet, J. (2002). Cathodically activated nucleophilic aromatic substitution of hydrogen: a novel electrochemical mechanism. Chemical communications (Cambridge, England), (22), 2638-9. https://doi.org/10.1039/b207168a
Gallardo, Iluminada, et al. "Cathodically activated nucleophilic aromatic substitution of hydrogen: a novel electrochemical mechanism." Chemical communications (Cambridge, England) vol. ,22 (2002): 2638-9. doi: https://doi.org/10.1039/b207168a
Gallardo I, Guirado G, Marquet J. Cathodically activated nucleophilic aromatic substitution of hydrogen: a novel electrochemical mechanism. Chem Commun (Camb). 2002 Nov 21;(22):2638-9. doi: 10.1039/b207168a. PMID: 12510275.
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Chem Commun (Camb). 2002 Nov 21;(22):2638-9. doi: 10.1039/b207168a.

Cathodically activated nucleophilic aromatic substitution of hydrogen: a novel electrochemical mechanism.

Chemical communications (Cambridge, England)

Iluminada Gallardo, Gonzalo Guirado, Jordi Marquet

Affiliations

  1. Departament de Química, Universitat Autònoma de Barcelona, 08193-Bellaterra Barcelona, Spain. [email protected]

PMID: 12510275 DOI: 10.1039/b207168a

Abstract

Cathodically activated nucleophilic aromatic substitution of hydrogen (SNArH) is reported for the first time; the 1,3,5-trinitrobenzene radical anion reacts with the nucleophile N-methylformamide leading to high yields of the sigma H-complex radical anion; this intermediate can be easily oxidised electrochemically by means of a three-electron mechanism giving rise to the nucleophilic aromatic substitution product (NASH product) in good yield.

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