Novel synthesis of a non-symmetric N¹CN²-Pd(II) pincer complex by a tandem reaction using a meta-hydroxylated imine ligand

The reflux reaction of ligand 3-[(2,4,6-trimethyl-phenylimino)-methyl]-phenol (1) with [Pd(NCPh)₂Cl₂] in toluene in presence of a base, results in the facile formation of the non-symmetric N¹CN²-Pd(II) pincer complex (2). The overall tandem reaction involves the benzonitrile activation at the nitrile moiety and a C-H activation process at the aromatic ring of (1) providing a pincer compound with one six and one five membered palladacycles, this structure was unequivocally confirmed by single crystal X-ray diffraction analysis. Complex (2) was used in Suzuki-Miyaura couplings demonstrating this compound to be an efficient catalyst for these transformations.