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

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

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
JournalPolyhedron
Volume100
DOIs
Publication statusPublished - 2015 Aug 4

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Palladium
carbenes
palladium
reactivity
Ligands
ligands
synthesis
Carbon Monoxide
Bearings (structural)
Maleic Anhydrides
Addition reactions
Styrene
Protonation
Maleic anhydride
anhydrides
carbene
styrenes
catalytic activity
Catalyst activity
Carbon

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

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title = "Palladium(0) complexes of N-heterocyclic carbene ligands with dangling NMeC=O functionalities: Synthesis, reactivity and application in Mizoroki-Heck reactions",
abstract = "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).",
author = "Jhou, {Yang Ming} and Debkumar Nandi and Lee, {Jhen Yi} and Tzeng, {Ru Jiun} and Lee, {Hon Man}",
year = "2015",
month = "8",
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Palladium(0) complexes of N-heterocyclic carbene ligands with dangling NMeC=O functionalities : Synthesis, reactivity and application in Mizoroki-Heck reactions. / Jhou, Yang Ming; Nandi, Debkumar; Lee, Jhen Yi; Tzeng, Ru Jiun; Lee, Hon Man.

In: Polyhedron, Vol. 100, 11413, 04.08.2015, p. 28-35.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Palladium(0) complexes of N-heterocyclic carbene ligands with dangling NMeC=O functionalities

T2 - Synthesis, reactivity and application in Mizoroki-Heck reactions

AU - Jhou, Yang Ming

AU - Nandi, Debkumar

AU - Lee, Jhen Yi

AU - Tzeng, Ru Jiun

AU - Lee, Hon Man

PY - 2015/8/4

Y1 - 2015/8/4

N2 - 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).

AB - 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).

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JF - Polyhedron

SN - 0277-5387

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