Jump to main content
Jump to site search

Issue 7, 2017
Previous Article Next Article

Green click synthesis of β-hydroxy-1,2,3-triazoles in water in the presence of a Cu(II)–azide catalyst: a new function for Cu(II)–azide complexes

Author affiliations

Abstract

A new Cu(II)–azide complex, [Cu(H2L)(N3)]·CH3OH (1), was synthesized by the reaction of Cu(NO3)2 3H2O with 2-{[(1E)-(2-hydroxyphenyl)methylene]amino}-2-methylpropane-1,3-diol (H3L) in the presence of an azide anion and a methanol solvent. The complex was characterized by elemental analysis and spectroscopic methods (FT-IR and UV-Vis), and its structure was determined by single crystal X-ray analysis. X-ray studies showed that the asymmetric unit of this compound is a mononuclear complex of Cu(II) which converts to a dinuclear one through end-to-end (EE)-azide bridges. Complex 1 was used as the catalyst for a three-component azide–epoxide–alkyne cycloaddition reaction in water as a green solvent. The effect of the amount of catalyst, temperature and also the coordinated azide on the cycloaddition reaction was studied and the products were characterized by FT-IR, NMR and single crystal X-ray analyses. At temperatures below 50 °C just one product formed while at higher temperatures two compounds were formed by the azide attack of the epoxide ring. The structural studies indicated that complex 1 converts to a tetranuclear Cu(II) complex, [Cu4(HL)4], after catalytic reaction in the absence of sodium azide. The results showed that complex 1 is an active catalyst for preparing 1,2,3-triazole based compounds containing primary and secondary alcoholic functionalities. Based on the obtained results, a mechanism was proposed for this catalytic reaction.

Graphical abstract: Green click synthesis of β-hydroxy-1,2,3-triazoles in water in the presence of a Cu(ii)–azide catalyst: a new function for Cu(ii)–azide complexes

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 09 Dec 2016, accepted on 23 Feb 2017, published on 24 Feb 2017 and first published online on 24 Feb 2017


Article type: Paper
DOI: 10.1039/C6NJ03865D
Citation: New J. Chem., 2017,41, 2658-2667
  •   Request permissions

    Green click synthesis of β-hydroxy-1,2,3-triazoles in water in the presence of a Cu(II)–azide catalyst: a new function for Cu(II)–azide complexes

    N. Noshiranzadeh, M. Emami, R. Bikas and A. Kozakiewicz, New J. Chem., 2017, 41, 2658
    DOI: 10.1039/C6NJ03865D

Search articles by author