Kumada−Corriu Reactions of Alkyl Halides with Alkynyl Nucleophiles

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Abstract

Pd₂(dba)₃−Ph₃P-catalyzed Kumada−Corriu coupling reactions of unactivated alkyl bromides or iodides with an alkynyl nucleophile furnish C_sp−C_sp3 bond formation. Alkynyl nucleophiles can be alkynyllithiums or the corresponding Grignard reagents. The superior performance of Ph₃P ligand over the trialkylphosphine ligands indicates that this cross-coupling reaction may be a reductive-elimination-controlled process.

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This article has been cited by 17 ACS Journal articles (5 most recent appear below).

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

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  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
• 

  Iron-Catalyzed Cross-Coupling Reactions between Arylzinc Reagents and Alkyl Halides Bearing β-Fluorines

  Xiaowei Lin, Feng Zheng, and Feng-Ling Qing
  Organometallics2011 Article ASAP

  • Iron-Catalyzed Cross-Coupling Reactions between Arylzinc Reagents and Alkyl Halides Bearing β-Fluorines

    Xiaowei Lin, Feng Zheng, and Feng-Ling Qing
    Organometallics2011 Article ASAP

    We report the first example of iron-catalyzed cross-coupling of α-halo-β,β-difluoroethylene-containing compounds with arylzinc reagents using TMEDA and dppp as coligands. The reaction affords a wide range of functional group tolerant gem-...

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

  Application of Stereoselective Ether Transfer to the Synthesis of Isotactic Polyethers

  Kai Liu, Joseph W. Arico and Richard E. Taylor
  The Journal of Organic Chemistry2010 75 (12), 3953-3957

  • Application of Stereoselective Ether Transfer to the Synthesis of Isotactic Polyethers

    Kai Liu, Joseph W. Arico and Richard E. Taylor
    The Journal of Organic Chemistry2010 75 (12), 3953-3957

    An efficient, convergent synthetic strategy has been developed which enables the synthesis of a series of naturally occurring isotactic polymethoxy compounds. Ether transfer followed by a hydride workup enables simultaneous, diastereoselective production ...

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

  Air-Stable Secondary Phosphine Oxide or Chloride (Pre)Ligands for Cross-Couplings of Unactivated Alkyl Chlorides

  Lutz Ackermann, Anant R. Kapdi and Carola Schulzke
  Organic Letters2010 12 (10), 2298-2301

  • Air-Stable Secondary Phosphine Oxide or Chloride (Pre)Ligands for Cross-Couplings of Unactivated Alkyl Chlorides

    Lutz Ackermann, Anant R. Kapdi and Carola Schulzke
    Organic Letters2010 12 (10), 2298-2301

    In situ generated and crystallographically well-defined, isolated palladium complexes derived from seven novel air-stable secondary phosphine oxides or chlorides enabled challenging Kumada−Corriu cross-couplings of unactivated alkyl chlorides bearing β-...

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

  Mild Room-Temperature Palladium-Catalyzed C3-Arylation of 2(1H)-Pyrazinones via a Desulfitative Kumada-Type Cross-Coupling Reaction

  Vaibhav P. Mehta, Sachin G. Modha and Erik Van der Eycken
  The Journal of Organic Chemistry2009 74 (17), 6870-6873

  • Mild Room-Temperature Palladium-Catalyzed C3-Arylation of 2(1H)-Pyrazinones via a Desulfitative Kumada-Type Cross-Coupling Reaction

    Vaibhav P. Mehta, Sachin G. Modha and Erik Van der Eycken
    The Journal of Organic Chemistry2009 74 (17), 6870-6873

    An efficient desulfitative Kumada-type cross-coupling protocol is reported for the C3-arylation of 5-chloro-3-(phenylsulfanyl)pyrazin-2(1H)-ones. The method has also been successfully extended to the arylation of some (hetero)aryl thioethers and ...

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

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