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

Floris Chevallier (1) , Thomas Blin (1) , Elisabeth Nagaradja (1) , Frédéric Lassagne (1) , Thierry Roisnel (1) , Yury S Halauko (2) , Vadim E Matulis (3) , Oleg A Ivashkevich (3) , Florence Mongin (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 Department of electrochemistry
3 Research Institute for Physico-Chemical Problems

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.

Domaines: Chimie organique; Chimie théorique et/ou physique

Floris Chevallier, Thomas Blin, Elisabeth Nagaradja, Frédéric Lassagne, Thierry Roisnel, et al.. Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles.. Organic & Biomolecular Chemistry, 2012, 10 (25), pp.4878-85. ⟨10.1039/c2ob25554e⟩. ⟨hal-01053777⟩