Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 13, Pages 6540-6549Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo400800j
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Funding
- European Regional Development Fund (ERDF)
- Galician Government [PGIDIT06PXIB203299PR]
- Consolidation Group Research Grant from Conselleria de Educacion (Xunta de Galicia)
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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 cydoaddition.
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