Journal
TETRAHEDRON
Volume 63, Issue 30, Pages 7097-7111Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.05.008
Keywords
green chemistry; supported phosphine ligands; soluble polymeric catalysts; highly active recoverable palladium catalyst; amination reaction; Suzuki reaction of aryl chlorides
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The so-called SPhos phosphine, an extremely active ligand in the amination and Suzuki coupling of sterically-hindered aryl chlorides, has been anchored on different supports such as non-soluble (cross-linked polystyrene) and soluble (non-cross-linked polystyrene and polyethyleneglycol) polymers, as well as high surface silica. SPhos anchored on polyethyleneglycol (PEG-SPhos) showed the best activity for both amination and Suzuki couplings. The PEG-SPhos ligand can be quantitatively recovered from the reaction mixture through precipitation with diethyl ether and recycled in four consecutive runs without loosing activity. P-31 NMR spectra of the reused anchored ligand showed that deactivation of the PEG-SPhos ligand comes from the progressive oxidation of the phosphine-to-phosphine oxide. (C) 2007 Elsevier Ltd. All rights reserved.
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