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- Title
Antagonistic Effect of Acetates in C-N Bond Formation with In Situ Generated Diazonium Salts: A Combined Theoretical and Experimental Study.
- Authors
Fabre, Indira; Perego, Luca Alessandro; Bergès, Julien; Ciofini, Ilaria; Grimaud, Laurence; Taillefer, Marc
- Abstract
The mechanism of the copper-catalyzed arylation of nitrogen heterocycles using anilines via diazonium salts has been studied by combining DFT and experimental data. A CuI/CuIII redox mechanism is proposed. Our study has revealed the multiple roles of the acid/base couple AcOH/AcO-. An in situ formed triazene species maintains a low concentration of diazonium salts in the reaction medium, which ensures limited formation of decomposition products. The results of DFT calculations have explained the lower reactivity of imidazole nucleophiles as compared with pyrazole in the arylation reaction.
- Subjects
HETEROCYCLIC compounds synthesis; NITROGEN compound synthesis; ACETATES; DIAZONIUM compounds; COPPER catalysts; ARYLATION; IMIDAZOLES; DENSITY functional theory
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 35, p5887
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600891