Copper-Catalyzed Huisgen 1,3-Dipolar Cycloaddition
under Oxidative Conditions: Polymer-Assisted Assembly of 4‑Acyl-1-Substituted-1,2,3-Triazoles
Posted on 2013-07-05 - 00:00
We
herein document the first example of a reliable copper-catalyzed Huisgen
1,3-dipolar cycloaddition under oxidative conditions. The
combined use of two polymer-supported reagents (polystyrene-1,5,7-triazabicyclo[4,4,0]dec-5-ene/Cu
and polystyrene-2-iodoxybenzamide) overcomes the thermodynamic
instability of copper(I) species toward oxidation, enabling the reliable
Cu-catalyzed Huisgen
1,3-dipolar cycloadditions in the presence of an oxidant agent. This
polymer-assisted pathway, not feasible under conventional homogeneous
conditions, provides a direct assembly of 4-acyl-1-substituted-1,2,3-triazoles,
contributing to expand the reliability and scope of Cu(I)-catalyzed
alkyne–azide
cycloaddition.
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Diz, Paula
M.; Coelho, Alberto; El Maatougui, Abdelaziz; Azuaje, Jhonny; Caamaño, Olga; Gil, Álvaro; et al. (2016). Copper-Catalyzed Huisgen 1,3-Dipolar Cycloaddition
under Oxidative Conditions: Polymer-Assisted Assembly of 4‑Acyl-1-Substituted-1,2,3-Triazoles. ACS Publications. Collection. https://doi.org/10.1021/jo400800j