Palladium Nanoparticles Immobilized on Poly(vinyl chloride)-Supported Pyridinium as an Efficient and Recyclable Catalyst for Suzuki-Miyaura Cross-Coupling Reaction

Bo Zhou,Yi-Qun Li

doi:10.1155/2011/313102

Abstract

The palladium nanoparticles immobilized on the polymeric surface of poly(vinyl chloride)-supported pyridinium (PVC-Py-Pd0) were achieved by a simple procedure by applying the corresponding functionalized polymer and palladium chloride in ethanol solution. The as-prepared catalyst (PVC-Py-Pd0) was found to be air and moisture stable and exhibits significant catalytic activity for Suzuki-Miyaura cross-coupling reaction of various aryl halides and phenylboronic acid under milder operating conditions. The procedure presented here showed several merits such as short reaction time, simple experimental and isolated procedure and excellent yields of products. Furthermore, the catalyst can be easily recovered and reused for at least six times with consistent activities.

Highlights

The palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acids, is one of the most powerful tool for the preparation of unsymmetrical biaryl compounds[1,2,3,4,5], which has been applied to many areas, including herbicides[6] and natural product syntheses[7,8,9]
To development of simple and reliable protocols for the immobilization of catalytically active palladium nanoparticles on functionalized Poly(vinyl chloride) (PVC), we report the synthesis and characterization of one kind of poly(vinyl chloride)–pyrudinium resin supported nanopalladium catalyst and the application of it in Suzuki-Miyaura reaction of aryl halides with arylboronic acids that can afford excellent yield in the air
To obtain the stable nanopalladium immobilized on the surface of polymer via electrosteric stabilization effects, we design a new polymer-supported pyridinium cation resin and use it as both steric and electrosteric stabilizing agents

Summary

Introduction

The palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acids, is one of the most powerful tool for the preparation of unsymmetrical biaryl compounds[1,2,3,4,5], which has been applied to many areas, including herbicides[6] and natural product syntheses[7,8,9]. Numerous efforts have been made to develop efficient catalyst systems for Suzuki-Miyaura cross-coupling reaction[10,11]. The traditional protocols for the Suzuki-Miyaura cross-coupling reaction prescribe a palladium species with phosphine ligands as the catalyst. Many immobilization methods and polymeric support materials used to catalyze the Suzuki-Miyaura reaction have been reported in literature[24,25,26,27]. To development of simple and reliable protocols for the immobilization of catalytically active palladium nanoparticles on functionalized PVC, we report the synthesis and characterization of one kind of poly(vinyl chloride)–pyrudinium resin supported nanopalladium catalyst and the application of it in Suzuki-Miyaura reaction of aryl halides with arylboronic acids that can afford excellent yield in the air. All of the products are known and the data are found to be identical with those that reported in literature elsewhere

Results and Discussion

29 O2N Br Cl

Conclusion