Polystyrene microsphere-immobilized palladium（II） porphyrin as mild, reusable, and highly efficient catalyst for Heck reaction

• Published in: 中国颗粒学报：英文版 2015 (5), p.128-133
• Main Author: Yinbin Huang Liangrong Yang Minghui Huang Jian Wang Lin XU Wensong Li Huacong Zhou Xitong Sun Huifang Xing Huizhou Liu
• Format: Article
• Language: English
• Subjects: 交联聚苯乙烯微球; 傅里叶变换红外光谱法; 催化剂回收; 卟啉; 可重复使用; 固定化; 电感耦合等离子体原子发射光谱; 钯（Ⅱ）
• ISSN: 1674-2001; 2210-4291

A novel Heck reaction catalyst consisting of a palladium（ll） complex of meso-tetra（p- hydroxyphenyl）porphyrin （MTP） and cross-linked chloromethylated polystyrene microspheres （PMs） was successfully prepared via covalent ether bonds between the chloride groups in the PMs and the hydroxyl groups in MTP. The catalyst was characterized using scanning electron microscopy, Fourier-transform infrared spectroscopy, and inductively coupled plasma atomic emission spectroscopy （ICP-AES）. This polystyrene-supported palladium-complex was an efficient heterogeneous catalyst for cross-coupling of aryl iodides with ethyl acrylate. The reaction of iodobenzene and ethyl acrylate under N2 at 100 °C and a catalyst concentration of 0.1% gave a gas chromatography product yield of 99.8%, which is much higher than that achieved using a free palladium（II） complex of MTP as the catalyst （41.3%）. The catalyst was recycled up to six times without significant loss of catalytic activity. These results suggest that the immobilized palladium（II） MTP catalyst has potential applications in synthetic and industrial chemistry.