Issue 25, 2012

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

Abstract

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

Supplementary files

Article information

Article type
Paper
Submitted
14 Mar 2012
Accepted
01 May 2012
First published
01 May 2012

Org. Biomol. Chem., 2012,10, 4878-4885

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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