Copper-Catalyzed Huisgen 1,3-Dipolar Cycloaddition under Oxidative Conditions: Polymer-Assisted Assembly of 4-Acyl-1-Substituted-1,2,3-Triazoles
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- 作者：Paula M. Diz ; Alberto Coelho ; Abdelaziz El Maatougui ; Jhonny Azuaje ; Olga Caama帽o ; 脕lvaro Gil ; Eddy Sotelo
- 刊名：The Journal of Organic Chemistry
- 出版年：2013
- 出版时间：July 5, 2013
- 年：2013
- 卷：78
- 期：13
- 页码：6540-6549
- 全文大小：429K
- 年卷期：v.78,no.13(July 5, 2013)
- ISSN：1520-6904
文摘
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鈥揳zide cycloaddition.