Pd^II Dispersed on Magnetic Partially Reduced GO/OMWCNT Non‐Covalently Modified with a Vic‐Dioxime: An Efficient and Magnetically Retrievable Catalyst for Suzuki‐Miyaura Coupling Reaction

Abstract

In the present study, a novel and magnetically separable Pd−catalyst system was designed using the immobilization of PdII on Phendioxime(PDO)‐functionalized magnetic partially reduced (GO‐OMWCNT) composite (MPR (GO‐OMWCNT)/PDO/PdII). In the as‐obtained nanocomposites, the incorporation of 1D OMWCNTs and 2D graphene oxide can form a versatile 3D network with high specific surface area and synergic properties. Moreover, non‐ covalent phendioxime functionalization provides highly effective functional groups on the surface of MPR (GO‐OMWCNT) for PdII. Non‐covalent interaction carries out through π‐π stacking and hydrogen bond interactions .The catalytic activity of this nanocomposite was examined in the Suzuki–Miyaura cross‐coupling reaction. MPR (GO‐OMWCNT)/PDO/PdII composite exhibited good catalytic efficiency and obtained the products in good to excellent yield under mild aerobic conditions. Moreover, the suggested catalyst could be easily recovered magnetically and used for at least six runs without a noticeable decrease in its catalytic activity.

Pd-Loaded Cellulose NanoSponge as a Heterogeneous Catalyst for Suzuki–Miyaura Coupling Reactions

“…By changing the halogen involved in the coupling reaction and considering Cl-benzene (entry 11) instead of Br-benzene (entry 8), we observed a decrease in yield from 93% to 55.5%. Once again, these values are in line with those reported for several heterogeneous supports [ 16 , 17 , 18 , 20 , 21 , 22 , 23 ].…”

“…These values are reasonably good and comparable to many industrial catalytic processes, but are obtained by operating in the presence of an eco-friendly cellulose-derived palladium support. In fact, while we are aware that higher TONs can be obtained under homogeneous conditions, these values are comparable or even better than those of most of the examples reported in the literature for fixing Pd on heterogeneous supports [ 16 , 17 , 18 , 20 , 21 , 22 , 23 ]. Moreover, in this case, the choice of the support falls on a bio-based system derived from waste biomass.…”

“…For these reasons, in recent years many solutions have been proposed for the immobilization of Pd(II)-precatalysts onto heterogeneous networks [ 16 , 17 , 18 , 19 ], also opening the route to continuous-flow synthetic processes [ 20 , 21 ]. However, in most cases the pre-functionalization of solid supports with proper ligands is necessary to guarantee high efficiency in fixing Pd(II), minimizing leaching phenomena [ 22 , 23 ]. Moreover, the increasing demand for bio-based materials derived from renewable sources, such as biomass waste, in the framework of the circular economy, pushes towards the design of new solutions as heterogenous supports for organometallic catalysis, capable of minimizing synthetic steps and providing sustainable solutions with low environmental impact.…”

Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

“…As other example of the coordinating ability of phendioxime, Shariatipour et al 826 have adsorbed phendioxime through the hydroxyl groups on partially reduced graphene oxide/oxidized multiwalled carbon nanotubes doped with Fe 3 O 4 magnetic particles, where Pd(II) ions are coordinated and catalyze the Suzuki−Miyaura cross-coupling reaction.…”

“…Phendione 867 is probably one of the most versatile building blocks ever used to functionalize phen. A plethora of articles describes the synthesis of 867 . ,,,− The common point to all the reported procedures is the strongly acidic (ensuring phen is protonated and increasing the solubility) and oxidizing conditions. Phendione can be further transformed into precious synthons for numerous applications.…”