Citation: Da Yang, Dongliang Wang, Huan Liu, Xiaoli Zhao, Yong Lu, Shijun Lai, Ye Liu. Ionic palladium complex as an efficient and recyclable catalyst for the carbonylative Sonogashira reaction[J]. Chinese Journal of Catalysis, ;2016, 37(3): 405-411. doi: 10.1016/S1872-2067(15)61022-1 shu

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

1.
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China

Corresponding author: Shijun Lai, Ye Liu,
Received Date: 2 November 2015
Available Online: 23 November 2015
Fund Project: 国家自然科学基金(21473058,21273077). (21473058,21273077)

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.
- Ionic phosphine ligand,
- Palladium complex,
- Carbonylative Sonogashira reaction,
- Ionic liquid
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