Polymer‐anchored copper(II) complex: an efficient reusable catalyst for the synthesis of propargylamines

Abstract

A new, heterogeneous, polymer‐supported copper(II) complex was prepared and characterized using various techniques, including Fourier transform infrared spectroscopy, scanning electron microscopy, energy dispersive X‐ray spectroscopy, atomic absorption spectroscopy and thermogravimetric analysis. This heterogeneous copper catalyst is efficient for the synthesis of propargylamines via a three‐component coupling reaction of aldehydes, amines and alkynes. The effect of solvent on the coupling reactions was investigated. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused for a minimum number of cycles without significant loss of its catalytic activity. Copyright © 2014 John Wiley & Sons, Ltd.

Recent Advances in C–C and C–N Bond Forming Reactions Catalysed by Polystyrene-Supported Copper Complexes

“…Propargylamines—which represent important intermediates for the synthesis of significant pharmaceutical polyfunctional substances—can be synthesized by the addition of alkynes on the imine bond ( Scheme 5 and Scheme 6 ) [ 22 , 23 , 24 , 25 , 26 ]. Propargylamines had been traditionally prepared by nucleophilic addition of magnesium or lithium acetylides on imines or their derivatives [ 22 ].…”

“…Unfortunately, the isolation of these homogeneous complexes from the reaction mixture as well as their recycling is unfeasible. Further facilitation started with the application of Cu(II) complexes immobilized on pearl-like polystyrene and with the reaction performed as a one-pot multi-component reaction [ 23 , 24 , 25 , 26 ]. Catalyst 9 was prepared by the reaction of l -proline with chloroacetylated pearl-like polystyrene and subsequent complexation with CuI ( Scheme 5 ) [ 23 ].…”

Solvent‐free synthesis of propargylamines catalyzed by an efficient recyclable ZnO‐supported CuO/Al2O3 nanocatalyst

“…According to previous reports, various metal‐based catalysts, including Ag, Fe, Li, Ni, Pd, In and Au, have been reported for the synthesis of propargylamines . In this view, copper and zinc catalysts are the most important for the synthesis of propargylamine derivatives, and good results have been achieved in the presence of these catalysts …”

Polymer supported copper(II) amine‐imine complexes in the C‐N and A3 coupling reactions

“…The polymer catalysts developed by this group were tested in the C‐N coupling reactions in which aryl iodides, aryl bromides, and boronic acids were used as arylation agents, and anilines, benzylamine, imidazole, phenols and tiophenols as nucleophilic reactants. Kodicherla et al described the use of the polymer supported copper catalyst based on the polystyrene bearing N,N‐dimethylethylenediamine as ligating groups . The catalyst was applied successfully in the A 3 coupling reactions between a series of aromatic aldehydes, secondary amines and phenylacetylene.…”

“…The catalyst was applied successfully in the A 3 coupling reactions between a series of aromatic aldehydes, secondary amines and phenylacetylene. It could also be recovered quantitatively by simple filtration and reused without a significant loss of its catalytic activity . Quite recently, Islam et al described the use of polymer supported copper(I) complex bearing glycine moieties as an efficient catalyst of A 3 coupling reactions .…”