Linear Polystyrene-Stabilized PdO Nanoparticle-Catalyzed Mizoroki-Heck Reactions in Water

Abstract

Linear polystyrene-stabilized PdO nanoparticles (PS-PdONPs) were prepared by thermal decomposition of Pd(OAc)2 in the presence of polystyrene. X-ray diffraction (XRD) and transmission electron microscopy (TEM) indicated the production of PdO nanoparticles. The loading of palladium was determined by inductively coupled plasma-atomic emission spectroscopy (ICP-AES). PS-PdONPs exhibited high catalytic activity for Mizoroki-Heck reactions under air in water and could be recycled without loss of activity.

Application of “Boomerang” Linear Polystyrene-Stabilized Pd Nanoparticles to a Series of C-C Coupling Reactions in Water

“…The Suzuki coupling reaction with 1-naphtylboronic acid and 2-thienylboronic acid gave the corresponding coupling products in 87 and 99% yields, respectively (Entries 11 and 12). As we reported earlier [32], PS-PdONPs showed low catalytic activity for the Heck reaction with styrene or bromobenzene. Therefore, we also examined the applicability of our boomerang system in the Heck reaction.…”

Recyclable Polymer‐Supported Nanometal Catalysts in Water

“…developed poly( N ‐vinyl‐2‐pyrrolidone)‐modified mesoporous carbon‐nanocage‐supported PdNPs that could be successfully used and recycled for Heck reactions under aerobic conditions . Thus, the catalytic utility of PS‐PdONPs had the potential to be applied to Heck reactions in water . The reaction of aryl iodides with acrylic acid occurred smoothly in water at 90 °C in 5 h to give trans ‐cinnamic acid derivatives in excellent yields (Fig.…”

“…[22a] Thus, the catalytic utility of PS-PdONPs had the potential to be applied to Heck reactions in water. [34] The reaction of aryl iodides with acrylic acid occurred smoothly in water at 90°C in 5 h to give transcinnamic acid derivatives in excellent yields (Fig. 5).…”

Nanocatalysts for the Heck Coupling Reactions

“…Other polymer-supported Pd complexes affording very high turnover frequencies were also reported recently. 144,145 For example, a poly(styrene-divinylbenzene)-supported Schiff base with Pd complexes was shown to give high turnover frequencies reaching up to 28,000 h −1 , along with very high selectivities with values more than 90%. 146 Besides Pd(II) complexes and Pd-NPs, PdO nanoparticles can be stabilized with polymers.…”

“…146 Besides Pd(II) complexes and Pd-NPs, PdO nanoparticles can be stabilized with polymers. 145 2.5 nm in diameter were synthesized within linear polystyrene by thermal decomposition of Pd(OAc) 2 (Figure 2.17). 147 The material was then successfully used as a catalyst for the Mizoroki-Heck reactions in aqueous solution.…”