Polymer Beads Decorated with Dendritic Systems as Supports for A3 Coupling Catalysts

Abstract

The gel type microscopic polymer beads bearing epoxy functionalities were modified using the two-stage procedures in order to decorate their surface with the moieties of the zeroth order PAMAM type dendrimer and different heterocyclic aldehydes (2-pyridinecarboxaldehyde, 2-pyrrolidinecarboxaldehyde, furfural or 2-thiophenecarboxaldehyde). The polymeric supports provided in this manner were then used for the immobilization of copper(II) ions. The resulting materials were characterized using different instrumental techniques (optical microscopy, SEM, FTIR microscopy, DR UV–Vis, ICP-OES, and thermal analysis). They were also used as catalysts in the model A3 coupling reaction of benzaldehyde, morpholine and phenylacetylene. The best catalytic activity was found for the polymeric catalyst bearing 2-pyridinecarboxaldehyde moieties. It turned out to be effective in the A3 coupling reactions included different benzaldehyde, alkyne, and secondary amine derivatives, as well. It could also be recycled several times without a significant decrease in its activity in the model A3 coupling reaction. Graphic Abstract

One-pot multicomponent polymerization towards heterocyclic polymers: a mini review

“…The polymeric catalysts with 2-pyridinecarboxaldehyde moieties effectively catalyzed these derivatives, and multiple recycling's of the material did not significantly impact its performance. 110 Zarei et al synthesized propargylamines on biochar@Cu–Ni nanocatalyst by A 3 coupling reactions between aldehydes, amines, and terminal alkynes employing pomegranate shells, biochar was prepared at 500 °C and coated with Cu–Ni nanoparticles. Using nanocatalysts and toluene as solvents, the highest efficiency was achieved at 80 °C.…”

Decorating polymer beads with 1014 inorganic-organic [2]rotaxanes as shown by spin counting

“…Beads functionalised with paramagnetic molecules have been used in catalysis 5 and studied as agents for dynamic nuclear polarisation (DNP) 6 . Further functionality has been introduced by blending these properties on or in polymer hosts, and such magnetic polymer beads have been exploited in many areas, including sensing, imaging and separations 7 .…”

CuSO4 nanoparticles loaded onto poly (toluenesulfonic acid‐formaldehyde)/polyethyleneimine composites: An efficient retrievable catalyst for A3/decarboxylative A3 reactions

“…Among the heterogeneous catalysts, because copper catalysts are low cost, readily available, and high active, some heterogenized copper salts and its complexes were successfully used to catalyze A 3 and decarboxylative A 3 couplings. These reported heterogeneous copper catalysts include Cu II @PAA/PVC mesoporous fibers, [ 11 ] polymer beads decorated with dendrimer supported Cu (II), [ 12 ] malachite, [ 13 ] Cu 0 NPs@CMC, [ 14 ] Fe 3 O 4 @SiO 2 ‐Se‐T/CuI, [ 15 ] fiber‐polyquaterniums@Cu(I), [ 16 ] PS‐PEG‐BPy‐CuBr 2, [ 17 ] Cu 0 @HAP@γ‐Fe 2 O 3, [ 18 ] chit@copper, [ 19 ] polymer‐supported copper (II) amine‐imine complexes, [ 20 ] Cu‐MOF‐74, [ 21 ] Cu (II)‐hydromagnesite, [ 22 ] CMC‐Cu II, [ 23 ] Cu@PMO‐IL, [ 24 ] GO‐CuCl 2, [ 25 ] Cu 0 ‐Mont, [ 26 ] CuSBA‐15, [ 27 ] Cu/Al/oxide mesoporous sponges, [ 28 ] Cu‐MOFs, [ 29 ] Cu (OH) x –Fe 3 O 4, [ 30 ] copper thin films, and [ 31 ] CuO NPs, [ 32 ] .…”