Synthesis of water soluble Pd-Piperidoimidazolin-2-ylidene complexes and their catalytic activities in neat water

Cakir S., TÜRKMEN H.

APPLIED ORGANOMETALLIC CHEMISTRY, vol.34, no.4, 2020 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 34 Issue: 4
  • Publication Date: 2020
  • Doi Number: 10.1002/aoc.5499
  • Title of Journal : APPLIED ORGANOMETALLIC CHEMISTRY

Abstract

Through the strategy of water soluble N-heterocyclic carbene (NHC) ligand, Pd-catalyzed reactions were developed in aqueous media. Therefore, four new piperidoimidazolinium salts (1a-d) consisting of sulfonate (a), esther (b, c) and carboxylic acid (d) functionalities and their water-soluble Pd-NHC complexes (2a-d) were synthesized. The new compounds were characterized by elemental analysis, FTIR, TGA, UV-vis and NMR spectroscopy. The catalytic activities of water soluble Pd-NHC complexes (2a-d) were investigated using the Suzuki-Miyaura (S-M) reaction and the reduction of nitroarenes. We found that the water-soluble polar or ionic groups on piperidoimidazolin-2-ylidine had an effect on the catalytic activity. The water-soluble catalyst can be recycled efficiently and reused six times with only a very slight loss of catalytic activity.