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Highly efficient structurally characterised novel precatalysts, di– and mononuclear heteroleptic Cu(I) dixanthate/xanthate–phosphine complexes for azide–alkyne cycloadditions

Abstract

Novel heteroleptic dinuclear, [Cu2(L)(PPh3)4] (L = 2,6-pyridinedimethyldixanthate L1 1, 1,4-benznedimethyldixanthate L2 2, 1,4-cyclohexanedixanthate L3 3) and mononuclear [Cu(L4)(PPh3)2] 4 (L4 = piperonylxanthate) and [Cu(L5)(dppf)] 5 (L5 = methylxanthate, dppf = 1,1'-bis(diphenylphosphino)ferrocene) complexes have been synthesized and characterized by elemental (C, H, N) analysis, high resolution mass spectrometry, (IR, UV–vis, 1H, 13C{1H} and 31P{1H} NMR) spectroscopy. Single crystal X-ray diffraction revealed S,S- bifunctional coordination of dixanthate group in dinuclear complexes 1–3 while 4 and 5 are mononuclear. Complexes 1–5 adopt tetrahedral coordination geometry about the copper atom. These precatalysts having two and one copper(I) centers in a single molecule have been applied in copper catalyzed azide–alkyne cycloaddition (CuAAC) reactions for the synthesis of variety of glycoconjugates triazoles under Click approach. Particularly the dinuclear catalyst 1, formed on the pyridyl linker based dixanthate ligand, displayed outstanding and reusable catalytic activity for this reaction. Full optimization of the reaction conditions demonstrated a noteworthy Click catalytic system with low catalyst loading under mild reaction conditions.

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Publication details

The article was received on 25 Mar 2019, accepted on 06 May 2019 and first published on 06 May 2019


Article type: Paper
DOI: 10.1039/C9NJ01551E
New J. Chem., 2019, Accepted Manuscript

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    Highly efficient structurally characterised novel precatalysts, di– and mononuclear heteroleptic Cu(I) dixanthate/xanthate–phosphine complexes for azide–alkyne cycloadditions

    A. Kushwaha, A. K. Agrihari, K. K. Manar, C. L. Yadav, V. K. K. TIWARI, M. G. B. Drew and N. Singh, New J. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9NJ01551E

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