Ethylenediamine-Functionalized Resin-Supported Pd(0) Complex: An Effective and Recyclable Catalyst for Heck Vinylation

✍ Scribed by Yuan-Fa Yang; Ming Zhuang; Chao-Xia Zeng; Chao-Biao Huang; Meng-Fei Luo

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 102 KB
• Volume: 24
• Category: Article
• ISSN: 0256-7660
• DOI: 10.1002/cjoc.200690244

✦ Synopsis

Abstract

The ethylenediamine‐functionalized resin‐supported Pd(0) complex was prepared from PdCl~2~ and ethylenediamine‐functionalized chloromethylated polystyrene, followed by reduction with KBH~4~. The complex was characterized by FT‐IR, XRD, BET, SEM and EDS. The resin‐supported catalyst exhibited high catalytic activity in the Heck reaction and could be reused up to 17 times in NMP or 16 times in DMF at 90 °C in the Heck reaction of iodobenzene with acrylic acid. The leaching investigation disclosed that the palladium leaching was caused by the interaction of iodobenzene with the metal Pd(0) on supported catalyst. The leached palladium species in filtrate was very stable and could be reused five times after the solid catalyst was filtered off. A cross‐transfer test in recycling in the presence of additional carbon disclosed that the soluble leached palladium species had much higher catalytic activity than supported and/or adsorbed palladium in solid‐solution heterogeneous Heck reaction.