Journal of Molecular Catalysis A-Chemical, Vol.418, 125-131, 2016
Palladium biphenyl N-heterocyclic carbene complexes: Synthesis, structure and their catalytic efficiency in water mediated Suzuki-Miyaura cross-coupling reaction
Synthesis of bis-N-heterocyclic carbene ligand with biphenyl backbone [MIBIPhen](Br)(2) (L), [Ag(MIBIPhen)](2)(PF6)(2) (1) and palladium-NHC complexes, [Pd(MIBIPhen)(Cl)(H3C-CN)]PF6 (2), [Pd(MIBIPhen)(H3C-CN)(2)](PF6)(2) (3) and [Pd(MIBIPhen)Br-2] (4) {MIBIPhen = (3,3'-(biphenyl-2,2'-diylbis(methylene))bis(1-methyl-1H-imidazol-3-ium)bromide]} is reported. All complexes (1-4) are characterized by NMR, ESI-MS, elemental analysis and single crystal XRD. Complex 1 serves as an efficient NHC transfer agent for the preparation of complex 2. Treatment of complex 2 with AgPF6 drives the exchange of chloride by acetonitrile to result in complex 3. Complex 4 is prepared by in situ deprotonation of MIBIPhen with Pd(OAc)(2). Complex 1 is molecular box type with silver in bent geometry. Complexes 2, 3 & 4 exist as monomers with palladium in distorted-square-planar geometry. All Pd-NHC complexes are explored as catalyst in water mediated Suzuki-Miyaura cross coupling reaction where complex 3 shows efficient catalytic activity. (C) 2016 Elsevier B.V. All rights reserved.