Efficient Cross-Coupling of Aryl Chlorides with Arylzinc Reagents Catalyzed by Amido Pincer Complexes of Nickel

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Abstract

The nickel-catalyzed Negishi cross-coupling reaction of aryl chlorides with arylzinc compounds was investigated. The nickel complexes with the amido pincer type of ligands exhibited high catalytic activity and good functional group tolerance.

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This article has been cited by 6 ACS Journal articles (5 most recent appear below).

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  Three-Coordinate Ni^II: Tracing the Origin of an Unusual, Facile Si−C(sp³) Bond Cleavage in [(^tBu₂PCH₂SiMe₂)₂N]Ni⁺

  Benjamin C. Fullmer, Hongjun Fan, Maren Pink, John C. Huffman, Nikolay P. Tsvetkov, and Kenneth G. Caulton
  Journal of the American Chemical Society2011 133 (8), 2571-2582

  • Three-Coordinate Ni^II: Tracing the Origin of an Unusual, Facile Si−C(sp³) Bond Cleavage in [(^tBu₂PCH₂SiMe₂)₂N]Ni⁺

    Benjamin C. Fullmer, Hongjun Fan, Maren Pink, John C. Huffman, Nikolay P. Tsvetkov, and Kenneth G. Caulton
    Journal of the American Chemical Society2011 133 (8), 2571-2582

    All attempts to synthesize (PNP)Ni(OTf) form instead (tBu2PCH2SiMe2NSiMe2OTf)Ni(CH2PtBu2). Abstraction of F− from (PNP)NiF by even a catalytic amount of BF3 causes rearrangement of the (transient) (PNP)Ni+ to analogous ring-opened [(tBu2PCH2SiMe2NSiMe2F)]...

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

  Palladium-Catalyzed Indole, Pyrrole, and Furan Arylation by Aryl Chlorides

  Enrico T. Nadres, Anna Lazareva, and Olafs Daugulis
  The Journal of Organic Chemistry2011 76 (2), 471-483

  • Palladium-Catalyzed Indole, Pyrrole, and Furan Arylation by Aryl Chlorides

    Enrico T. Nadres, Anna Lazareva, and Olafs Daugulis
    The Journal of Organic Chemistry2011 76 (2), 471-483

    The palladium-catalyzed direct arylation of indoles, pyrroles, and furans by aryl chlorides has been demonstrated. The method employs a palladium acetate catalyst, 2-(dicyclohexylphosphino)-biphenyl ligand, and an inorganic base. Electron-rich and ...

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

  N-Heterocyclic Carbene-Based Nickel Complexes: Synthesis and Catalysis in Cross-Couplings of Aryl Chlorides with ArMX (M = Mg or Zn)

  Cheng Zhang and Zhong-Xia Wang
  Organometallics2009 28 (22), 6507-6514

  • N-Heterocyclic Carbene-Based Nickel Complexes: Synthesis and Catalysis in Cross-Couplings of Aryl Chlorides with ArMX (M = Mg or Zn)

    Cheng Zhang and Zhong-Xia Wang
    Organometallics2009 28 (22), 6507-6514

    Two C,N,N-chelate nickel complexes, [Ni(Cl){2-(CN(Me)(CH)2N)C6H4N═P(Ph2)CH2Pyr}]+I− and [Ni(Cl){2-(CN(Pri)(CH)2N)C6H4N═P(Ph2)CH2P(Ph2)═NC6H4Me-4}]+I−, were synthesized by reaction of (DME)NiCl2 (DME = 1,2-dimethoxyethane) with 2-(CN(R)(CH)2N)C6H4N═P(Ph2)...

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

  Synthesis and Characterization of Amido Pincer Complexes of Lithium and Nickel and Catalysis of the Nickel Complexes in the Kumada Cross-Coupling

  Kai Sun, Li Wang and Zhong-Xia Wang
  Organometallics2008 27 (21), 5649-5656

  • Synthesis and Characterization of Amido Pincer Complexes of Lithium and Nickel and Catalysis of the Nickel Complexes in the Kumada Cross-Coupling

    Kai Sun, Li Wang and Zhong-Xia Wang
    Organometallics2008 27 (21), 5649-5656

    P,N,P- and N,N,P-chelate ligands and their complexes of lithium and nickel were synthesized and characterized. Some of the nickel can efficiently catalyze cross-coupling reactions of unactivated and deactivated aryl chlorides with aryl Grignard reagents.

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

  Efficient Negishi Coupling Reactions of Aryl Chlorides Catalyzed by Binuclear and Mononuclear Nickel−N-Heterocyclic Carbene Complexes

  Zhenxing Xi, Yongbo Zhou and Wanzhi Chen
  The Journal of Organic Chemistry2008 73 (21), 8497-8501

  • Efficient Negishi Coupling Reactions of Aryl Chlorides Catalyzed by Binuclear and Mononuclear Nickel−N-Heterocyclic Carbene Complexes

    Zhenxing Xi, Yongbo Zhou and Wanzhi Chen
    The Journal of Organic Chemistry2008 73 (21), 8497-8501
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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