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

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.