A soluble polyethyleneglycol-anchored phosphine as a highly active, reusable ligand for Pd-catalyzed couplings of aryl chlorides: comparison with cross and non-cross-linked polystyrene and silica supports

作者：Leyva Antonio; Garcia Hermenegildo^*; Corma Avelino

来源：Tetrahedron, 2007, 63(30): 7097-7111.

DOI：10.1016/j.tet.2007.05.008

• green chemistry
• supported phosphine ligands
• soluble polymeric catalysts
• highly active recoverable palladium catalyst
• amination reaction
• Suzuki reaction of aryl chlorides

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. (31)P 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.

• 出版日期2007-7-23