Palladium nanoparticles supported on modified polystyrene resin as a polymeric catalyst for Sonogashira--Hagihara coupling reactions

Abstract

Pd(0) nanoparticles supported on modified crosslinked polystyrene were synthesized and characterized.Crosslinked polystyrene was reacted with trioxane and chlorotrimethylsilane in the presence of SnCl 4 to form Merrifield resin. The Merrifield resin was then converted to polymer-bound β -aminoalcohol and subsequently to βaminophosphinite ligand. This polymeric ligand was reacted with PdCl 2 to obtain a polymeric Pd(0) complex. The TEM image of the Pd catalyst showed good dispersion of catalytic sites. The Pd catalyst exhibits excellent activity and stability in copper-free Sonogashira-Hagihara cross-coupling reactions under aerobic conditions. This protocol can be applied efficiently to the coupling reactions of chloro-as well as iodo-and bromo-arenes. The catalyst can be reused several times without any considerable decrease in its activity.

BNPs@SiO2(CH2)3 -TAPC-O-(CH2)2NH2-Pd (0) as a Nanocatalyst for the Coupling Reactions and Removing of Organic Dyes

“…Up to now, various methods containing intermediate metals such as Mn (III/IV), Fe(III), Co(III), Ni(II), Co (II) and palladium have been documented in the literature for Suzuki and Heck reactions [16][17][18][19][20][21][22][23] . Numerous solid-supports like Fe 3 O 4 24 , Nano-Silica (Pdnp-nSTDP) 25 , MCM41 26 , SBA-15 27 , polymers 28,29 , TiO 2 NPs 30 , polystyrene nano bers 31 , magnetic polymers 32 , mesoporous and C60 33,34 and magnetic-boehmite 35 have been used to prepare of pd-nano-catalysts.…”

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

“…Thus, PdNPs supported on a crosslinked polystyrene 1 ( Figure 1) were used as catalyst in the copper-free Sonogashira coupling of phenylacetylene with aryl iodides, bromides and chlorides (Scheme 2), the addition of tetra-n-butylammonium bromide (TBAB) as nanoparticle stabilizer being necessary in the case of aryl chlorides [14]. The catalyst was recovered by filtration and reused up to five times in the model reaction between iodobenzene and phenylacetylene obtaining recycling yields ranging from 88% to 72%.…”

Facile in-situ synthesis and deposition of monodisperse palladium nanoparticles on polydopamine-functionalized silica gel as a heterogeneous and recyclable nanocatalyst for aerobic oxidation of alcohols

“…Heterogeneous Pd catalysts can overcome these limitations efficiently, though they are not as active as homogeneous catalysts due to the disfavored kinetics of biphasic catalytic systems. Therefore, Pd species are usually anchored on a solid support matrix with high specific surface area to increase the number of collisions between Pd particles and the substrates [20][21][22][23][24]. Leaching of Pd during catalysis is another disadvantage of Pd heterogeneous catalysis.…”