Ionic palladium complex as an efficient and recyclable catalyst for the carbonylative Sonogashira reaction

The neutral palladium(II) complex bis-[1-(5’-diphenylphosphinothiazol-2’-yl)-imidazolyl] dichloropalladium(II) (1A) ligated by thiazolylimidazolyl-based phosphine (L1) in which thiazolylimidazolyl acted as an S- and N-donor provider with weak coordinating nature, and the ionic complex bis-[1-(5’-diphenylphosphinothiazol-2’-yl)-3-methylimidazolium] dichloropalladium(II) trifluoromethanesulfonate (2A) ligated by thiazolylimidazolium-based phosphine (L2) after quaternization of L1 using methyl trifluoromethanesulphonate were synthesized. It was found that the introduced positive charges and strong electron-withdrawing effect in 2A not only led to changes in the configuration and structural stability of the complex, but also lowered its catalytic performance in carbonylative Sonogashira reactions. These effects reveal the important role of the N-donor in 1A. In addition, as an ionic palladium complex, 2A combined with the room-temperature ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate could be recycled eight times as the catalyst in carbonylative Sonogashira reactions without detectable metal leaching.

Graphical AbstractAn ionic palladium complex was prepared through complexation of bis(acetonitrile)palladium(II) chloride with an ionic phosphine as an efficient and recyclable catalyst for the carbonylative Sonogashira reaction.Figure optionsDownload as PowerPoint slide