Assembled catalyst of palladium and non-cross-linked amphiphilic polymer ligand for the efficient heterogeneous Heck reaction

The efficient heterogeneous Heck reaction was achieved by a new networked and supramolecular catalyst PdAS-V (1b). Employing of PdAS-V in 5.0X10(-5) mol equiv. efficiently progressed the heterogeneous Heck reaction of a series of aryl iodides with acrylates. styrenes and acrylic acid. PdAS-V was successfully recycled five times without any decrease in its activity, and showed good stability in toluene and water, and hence the Heck reaction was efficiently performed in both reaction media. The use of 8.0X10(-7) mol equiv. of PdAS-V resulted in the coupling product in 92% yield with the turnover number (TON) and the turnover frequency (TOF) of PdAS-V reached up to 1,150,000 and 12,000, respectively. The efficient synthesis of resveratrol was achieved via the PdAS-V-promoted Heck reaction. (C) 2004 Elsevier Ltd. All rights reserved.