Imidazolium salicylaldimine frameworks for the preparation of tridentate N-heterocyclic carbene ligands

Sterically hindered salicylaldimine functionalized imidazolium salts 2 have been prepared. The structures of the synthesized compounds were determined by spectroscopic techniques. The reaction of these salts containing arylmethyl-N chain (aryl: phenyl (2a), 2,4,6-trimethylphenyl (2b), 2,3,4,5,6-pentamethylphenyl (2c)) with Pd(OAc)2 in boiling toluene afforded Pd(II) complexes 3 in high yields. The X-ray structure of 1-[3-(3,5-di-tert-butyl-2-oxophenyl)propyliminato]-3-(2,4,6-trimethylbenzyl)imidazol-2-ylidenebromopalladium(II) (3b) has been determined. The Suzuki–Miyaura reaction was used to investigate their activity as catalysts either prepared in situ or from well-defined complexes. They are efficient when activated arylbromides are used as substrates.

Graphical abstractSterically hindered salicylaldimine functionalized imidazolium salts 2 have been prepared. The structures of the synthesized compounds were determined by spectroscopic techniques. The reaction of these salts containing arylmethyl-N chain (aryl: phenyl (2a), 2,4,6-trimethylphenyl (2b), 2,3,4,5,6-pentamethylphenyl (2c)) with Pd(OAc)2 in boiling toluene afforded Pd(II) complexes 3 in high yields. The X-ray structure of 1-[3-(3,5-di-tert-butyl-2-oxophenyl)propyliminato]-3-(2,4,6-trimethylbenzyl)imidazol-2-ylidenebromopalladium(II) (3b) has been determined. The Suzuki–Miyaura reaction was used to investigate their activity as catalysts either prepared in situ or from well-defined complexes. They are very efficient when activated arylbromides are used as substrates.Figure optionsDownload full-size imageDownload as PowerPoint slide