Pyridinyl-triazole ligand systems for highly efficient CuI-catalyzed azide-alkyne cycloaddition

Pyridinyl-triazole ligand systems (including N2-2-pyridinyl 1,2,3-triazoles and N1/N2-substituted 2-(NH-1,2,3-triazol-4-yl)pyridines) were found to be superior ligands for CuI-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. Low catalyst loadings, short reaction times, facile catalyst recycla...

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Veröffentlicht in:Catalysis communications 2021-01, Vol.148, p.106165, Article 106165
Hauptverfasser: Zheng, Lei, Wang, Ye, Meng, Xianggao, Chen, Yunfeng
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Sprache:eng
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Zusammenfassung:Pyridinyl-triazole ligand systems (including N2-2-pyridinyl 1,2,3-triazoles and N1/N2-substituted 2-(NH-1,2,3-triazol-4-yl)pyridines) were found to be superior ligands for CuI-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. Low catalyst loadings, short reaction times, facile catalyst recyclability, ambient temperature, and open-flask conditions made this catalytic system very practical. The iodide anions could form iodine bridges to construct stable dinuclear Cu(I) complexes with these ligands, which was the key to achieve high catalytic activities. While CuBr and CuCl were not suitable for this ligand system because of the improper size of Br and Cl atoms for the formation of the corresponding dinuclear Cu(I) complexes. [Display omitted] •A simple pyridinyl-triazole ligand system for CuI-catalyzed AAC reactions.•Dinuclear Cu(I) complex with [Cu2(μ-I)2] core as efficient catalysis.•Simple and mild reaction conditions and facile recyclable catalyst.
ISSN:1566-7367
1873-3905
DOI:10.1016/j.catcom.2020.106165