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Issue 25, 2012
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Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles

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2-Aryl-1,2,3-triazoles were synthesized by cyclization of the corresponding glyoxal arylosazones, generated from commercial arylhydrazines. The deproto-metallation of 2-phenyl-1,2,3-triazole was attempted using different 2,2,6,6-tetramethylpiperidino-based mixed lithium–metal (Zn, Cd, Cu, Co, Fe) combinations, giving results in the case of Zn, Cd, and Cu. The lithium–zinc combination was next selected to apply the deprotonation–iodination sequence to all the 2-aryl-1,2,3-triazoles synthesized. The results were analyzed with the help of the CH acidities of the substrates, determined in THF solution using the DFT B3LYP method.

Graphical abstract: Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles

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Publication details

The article was received on 14 Mar 2012, accepted on 01 May 2012 and first published on 01 May 2012

Article type: Paper
DOI: 10.1039/C2OB25554E
Citation: Org. Biomol. Chem., 2012,10, 4878-4885
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    Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles

    F. Chevallier, T. Blin, E. Nagaradja, F. Lassagne, T. Roisnel, Y. S. Halauko, V. E. Matulis, O. A. Ivashkevich and F. Mongin, Org. Biomol. Chem., 2012, 10, 4878
    DOI: 10.1039/C2OB25554E

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