Highly efficient and recyclable pre-catalysts based on mono- and dinuclear heteroleptic Cu(I) dithio- PPh3 complexes to produce variety of glycoconjugate triazoles

Abstract

Highly efficient and reusable pre-formed mono- and dinuclear heteroleptic copper(I) dithiocarbamate and dithiocarbimate complex based catalysts, [Cu(PPh3)2(L)] and [Cu2(PPh3)4(L)] (L = N-(4-methylpyridyl)-N-(3-methylpyridyl)dithiocarbamate− L1 1, N-methylfuryl-N-methylthiophenedithiocarbamate- L2 2; 4-chlorobenzenesulfonyl dithiocarbimate2- L3 3, 4-bromobenzenesulfonyldithiocarbimate2- L4 4) have been utilized in the cycloaddition reactions of azide and alkyne to form a variety of glycoconjugate triazoles in Click chemistry. These new pre-catalysts have been characterized by elemental (C, H, N) analysis, IR, UV–vis., 1H, 13C{1H}, and 31P{1H} NMR spectroscopy and their structures have been revealed by X-ray crystallography. In the structures of (1,2)/(3,4) the copper atoms are situated within a four coordinate (P2S2)/(P2NS) distorted tetrahedral geometry. Notably in the dinuclear complexes 3 and 4, the dithiocarbimate ligands are bonded in a S, S- chelating mode to one copper atom and simultaneously bridge the other copper centre via N, S- donor atoms. 1-4 are strongly luminescent in CH2Cl2 solution at room temperature. © 2019 Elsevier B.V.