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

Chavan, Sanjay ; Devkule, Shilpa

Abstract

Abstract

A 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 = ClO4-, BF4- and PF6- ) with N-(2-quinolinylmethylene)-1,5-dimethyl-2-phenyl-1-pyrazole-3-(2H)-one (L) in presence of triphenyl- phosphine (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 were tested as catalyst for Sonogashira cross-coupling of phenylacetylene with aryl iodide. The results showed that all complexes worked as an effective catalyst at low temperature yielded substituted aryl alkynes as a product. The nature of phosphine ligands and size of counter anions shows marked effect on their catalytic properties of all the complexes.


Keyword(s)

Copper catalyst, Arylated alkynes, Sonogashira coupling


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