Synthesis, structural characterization and catalytic activity of a palladium(II) complex bearing a new ditopic thiophene-N-heterocyclic carbene ligand

A new thiophene-functionalized benzimidazolium salt (2) has been prepared by reacting N-methylbenzimidazole with 2-bromomethylthiophene (1), which in turn was obtained by bromination of 2-thiophenemethanol with PBr3. Subsequent reaction of salt 2 with Pd(OAc)2 afforded the cis-configured bis(carbene) Pd(II) complex (cis-3), which in solution exists as an inseparable mixture of cis–anti and cis–syn-rotamers in a 3.5:1 ratio. All new compounds have been fully characterized by spectroscopic and spectrometric methods. A preliminary catalytic study shows that cis-3 is highly active in the Suzuki–Miyaura coupling of aryl bromides with phenylboronic acid in/on water as environmentally benign reaction media.