Copper(I) complexes with N-(2-quinolinylmethylene)-1, 5-dimethyl- 2-phenyl-1-pyrazole-3-(2H)-one and phosphine as ligands: Effective catalyst for Sonogashira cross-coupling reaction
598-607A new series of copper(I) complexes of the type [Cu(L)(PPh3)2]X (1a-c) and [Cu(L)(dppe)]X (2a-c) have been prepared by the reaction of Cu(MeCN)4]X (where X = ClO, BF and PF) with N-(2-quinolinylmethylene)-1,5-dimethyl-2-phenyl-1-pyrazole-3-(2H)-one (L) in presence of triphenylphosphine (PPh3) or 1,2-bis(diphenylphosphino)ethane (dppe) as an ancillary ligand. The UV-visible spectra indicate that, the ancillary phosphine ligands significantly perturb the MLCT state of copper(I) complexes. The thermally stable 1a-c and 2a-c complexes exhibit quasireversible redox behaviour corresponding to Cu(I)/Cu(II) couple. All complexes are tested as catalyst for Sonogashira cross-coupling of phenylacetylene with aryl iodide. The results show that all complexes worked as an effective catalyst at low temperature yielding substituted aryl alkynes as a product. The nature of phosphine ligands and size of counter anions shows marked effect on catalytic properties of all the complexes
