Room-Temperature Kumada Cross-Coupling of Unactivated Aryl Chlorides Catalyzed by N-Heterocylic Carbene-Based Nickel(II) Complexes

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Abstract

The Kumada cross-coupling reaction of a variety of unactivated aryl chlorides, vinyl chlorides, and heteroaryl chlorides catalyzed by nickel(II) complexes containing pyridine-functionalized NHC ligands is described. The catalysts are so active that the reactions proceed at room temperature in excellent yields.

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This article has been cited by 30 ACS Journal articles (5 most recent appear below).

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  Synthesis and Catalytic Activity in Suzuki Coupling of Nickel Complexes Bearing n-Butyl- and Triethoxysilylpropyl-Substituted NHC Ligands: Toward the Heterogenization of Molecular Catalysts

  Anna Magdalena Oertel, Vincent Ritleng, and Michael J. Chetcuti
  Organometallics2012 Article ASAP

  • Synthesis and Catalytic Activity in Suzuki Coupling of Nickel Complexes Bearing n-Butyl- and Triethoxysilylpropyl-Substituted NHC Ligands: Toward the Heterogenization of Molecular Catalysts

    Anna Magdalena Oertel, Vincent Ritleng, and Michael J. Chetcuti
    Organometallics2012 Article ASAP

    Cyclopentadienyl N-heterocyclic carbene (NHC) nickel complexes of general formula [Ni(R-NHC-nBu)XCp] [R-NHC-nBu = 1-butyl-3-methyl-, 1-isopropyl-3-butyl-, 1-phenyl-3-butyl-, 1-(2,4,6-trimethylphenyl)-3-butyl-, 1-(2,6-diisopropylphenyl)-3-butyl-imidazol-2-...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Synthesis and Structural Characterization of Half-Sandwich Nickel Complexes Bearing Two Different N-Heterocyclic Carbene Ligands

  Anna Magdalena Oertel, Vincent Ritleng, Loïc Burr, and Michael J. Chetcuti
  Organometallics2011 30 (24), 6685-6691

  • Synthesis and Structural Characterization of Half-Sandwich Nickel Complexes Bearing Two Different N-Heterocyclic Carbene Ligands

    Anna Magdalena Oertel, Vincent Ritleng, Loïc Burr, and Michael J. Chetcuti
    Organometallics2011 30 (24), 6685-6691

    Cationic cyclopentadienyl mixed bis-N-heterocyclic carbene (NHC) nickel complexes of the general formula [Ni(NHC)(NHC′)Cp](PF6) (NHC/NHC′ = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (Mes2NHC) a, 1,3-dimethylimidazol-2-ylidene (Me2NHC) b, 1-...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Kumada Coupling of Aryl, Heteroaryl, and Vinyl Chlorides Catalyzed by Amido Pincer Nickel Complexes

  Ning Liu and Zhong-Xia Wang
  The Journal of Organic Chemistry2011 76 (24), 10031-10038

  • Kumada Coupling of Aryl, Heteroaryl, and Vinyl Chlorides Catalyzed by Amido Pincer Nickel Complexes

    Ning Liu and Zhong-Xia Wang
    The Journal of Organic Chemistry2011 76 (24), 10031-10038

    A series of amido pincer complexes of nickel were examined for their catalysis in the Kumada cross-coupling reaction. The P,N,O-pincer nickel complexes tested are active catalysts for the cross-coupling of aryl, heteroaryl, and vinyl chlorides with aryl ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Half-Sandwich Ruthenium(II) Picolyl-NHC Complexes: Synthesis, Characterization, and Catalytic Activity in Transfer Hydrogenation Reactions

  Francys E. Fernández, M. Carmen Puerta, and Pedro Valerga
  Organometallics2011 30 (21), 5793-5802

  • Half-Sandwich Ruthenium(II) Picolyl-NHC Complexes: Synthesis, Characterization, and Catalytic Activity in Transfer Hydrogenation Reactions

    Francys E. Fernández, M. Carmen Puerta, and Pedro Valerga
    Organometallics2011 30 (21), 5793-5802

    Pentamethylcyclopentadienyl ruthenium(II) complexes with picolyl-functionalized N-heterocyclic carbenes [(η5-C5Me5)Ru(L)(CH3CN)][PF6] (L = 3-methyl-1-(2-picolyl)imidazol-2-ylidene (1a), 3-isopropyl-1-(2-picolyl)imidazol-2-ylidene (1b), 3-phenyl-1-(2-...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  C‒H Functionalization polycondensation of chlorothiophenes in the presence of nickel catalyst with stoichiometric or catalytically-generated magnesium amide

  Shunsuke Tamba , Keisuke Shono , Atsushi Sugie , and Atsunori Mori
  Journal of the American Chemical Society 0 (ja),

  • C‒H Functionalization polycondensation of chlorothiophenes in the presence of nickel catalyst with stoichiometric or catalytically-generated magnesium amide

    Shunsuke Tamba , Keisuke Shono , Atsushi Sugie , and Atsunori Mori
    Journal of the American Chemical Society 0 (ja),

    Polymerization of 2-chloro-3-substituted thiophenes proceeded with a stoichiometric amount of magnesium amide TMPMgCl•LiCl or a combination of a Grignard rea-gent and a catalytic amount of secondary amine in the presence of a nickel catalyst. Although the ...

    Abstract | Hi-Res PDF | PDF w/ Links

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