Palladium(0) complexes of N-heterocyclic carbene ligands with dangling NMeC=O functionalities: Synthesis, reactivity and application in Mizoroki-Heck reactions

Yang Ming Jhou, Debkumar Nandi, Jhen Yi Lee, Ru Jiun Tzeng, Hon Man Lee

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Abstract A series of new Pd(0) complexes of N-heterocyclic carbene (NHC) ligands with dangling NMe(CO) functionalities (LMe) is reported, with yields in the range 56-73%. The reactivity of one of the Pd(0) complexes, bearing bulky N-mesityl groups, towards the oxidative addition of pentafluoroiodobenzene was studied, revealing the formation of decafluorobiphenyl, a diiodo Pd(II) NHC complex and an intriguing Pd(II) complex with four carbon-donor ligands coordinated to the metal center. The latter complex contains two new NHC ligands derived from LMe. One of the NHC ligands is a bidentate ligand, resulting from an addition reaction between LMe and the coordinated maleic anhydride. The other NHC ligand is derived from the N-protonation of LMe. A pentafluorophenyl ligand completes the fourth coordination site. A mechanism for the formation of this intriguing Pd(II) complex is proposed. The structures of these two new Pd(II) complexes were established by single-crystal X-ray diffraction studies. The catalytic activities of the new Pd(0) complex with LMe in the Mizoroki-Heck coupling reaction between 4-chloroacetophenone and styrene were compared and they contrast with those reported for the Pd(0) NHC complex with dangling NH(CO) groups (LH).

Original languageEnglish
Article number11413
Pages (from-to)28-35
Number of pages8
Publication statusPublished - 2015 Aug 4


All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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