Issue 10, 2012

An efficient and recyclable dendritic catalyst able to dramatically decrease palladium leaching in Suzuki couplings

Abstract

A series of novel monomeric and dendritic thiazolyl phosphines (generations 1 and 3) was prepared and the activity these ligands conferred to palladium in Suzuki couplings was evaluated. The heteroaryl ligands were revealed to be very efficient and were able to perform the reactions in mild conditions. Besides, their efficiency was compared to that of the corresponding triphenylphosphines. Moreover, the possibility to reuse both families of dendritic ligands was explored and the thiazolyl phosphine-based catalytic systems could be successfully recycled for five consecutive reactions without loss of activity, contrary to their triphenylphosphine counterparts. Remarkably, the palladium leaching was found to be dramatically reduced by using the dendrimer-supported thiazolylphosphines instead of the monomeric ligand and only trace amounts of metal (<0.55 ppm) could be found in the coupling product before any purification.

Graphical abstract: An efficient and recyclable dendritic catalyst able to dramatically decrease palladium leaching in Suzuki couplings

Supplementary files

Article information

Article type
Paper
Submitted
29 May 2012
Accepted
19 Jul 2012
First published
24 Jul 2012

Green Chem., 2012,14, 2807-2815

An efficient and recyclable dendritic catalyst able to dramatically decrease palladium leaching in Suzuki couplings

M. Keller, A. Hameau, G. Spataro, S. Ladeira, A. Caminade, J. Majoral and A. Ouali, Green Chem., 2012, 14, 2807 DOI: 10.1039/C2GC35832H

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