Copper-Catalyzed Coupling of Imines, Acid Chlorides, and Alkynes:  A Multicomponent Route to Propargylamides

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Abstract

The use of imines in a metal-catalyzed coupling with alkynes and acid chlorides is described. This process proceeds rapidly with CuI as the catalyst and provides an efficient and general three-component coupling method to prepare propargylamides. The coupling can also be diversified to allow the formation of N-carbamate-protected propargylamines with the use of chloroformates.

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This article has been cited by 25 ACS Journal articles (5 most recent appear below).

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  Copper-Catalyzed Petasis-Type Reaction: A General Route to α-Substituted Amides From Imines, Acid Chlorides, and Organoboron Reagents

  Marie S. T. Morin, Yingdong Lu, Daniel A. Black, and Bruce A. Arndtsen
  The Journal of Organic Chemistry2012 Article ASAP

  • Copper-Catalyzed Petasis-Type Reaction: A General Route to α-Substituted Amides From Imines, Acid Chlorides, and Organoboron Reagents

    Marie S. T. Morin, Yingdong Lu, Daniel A. Black, and Bruce A. Arndtsen
    The Journal of Organic Chemistry2012 Article ASAP

    A copper-catalyzed Petasis-type reaction of imines, acid chlorides, and organoboranes to form α-substituted amides is described. This reaction does not require the use of activated imines or the transfer of special units from the organoboranes and ...

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

  One-Pot Zn/CuI/TFA-Catalyzed Domino Three-Component–Carbocyclization Reaction Involving Biphenyl-2-carbaldehydes/Alkynes/Piperidine: Allenes-Mediated Construction of Phenanthrenes

  Mohammad Saifuddin, Piyush K. Agarwal, and Bijoy Kundu
  The Journal of Organic Chemistry2011 76 (24), 10122-10128

  • One-Pot Zn/CuI/TFA-Catalyzed Domino Three-Component–Carbocyclization Reaction Involving Biphenyl-2-carbaldehydes/Alkynes/Piperidine: Allenes-Mediated Construction of Phenanthrenes

    Mohammad Saifuddin, Piyush K. Agarwal, and Bijoy Kundu
    The Journal of Organic Chemistry2011 76 (24), 10122-10128

    A one-pot protocol involving Zn/CuI/TFA-catalyzed domino three-component and subsequent carbocyclization reactions is described. The reaction proceeds via formation of propargyl amines from biphenyl-2-carbaldehydes/terminal alkynes/piperidine followed by ...

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

  Facile Synthesis of Tetrahydro-1H-isoindolones via a Sequential Three-Component Copper-Catalyzed Coupling/Propargyl-Allenyl Isomerization/[4 + 2] Cyclization Reaction

  Jian Cao and Xian Huang
  Organic Letters2010 12 (21), 5048-5051

  • Facile Synthesis of Tetrahydro-1H-isoindolones via a Sequential Three-Component Copper-Catalyzed Coupling/Propargyl-Allenyl Isomerization/[4 + 2] Cyclization Reaction

    Jian Cao and Xian Huang
    Organic Letters2010 12 (21), 5048-5051

    An interesting sequential three-component copper-catalyzed coupling/propargyl-allenyl isomerization/[4 + 2] cyclization reaction, providing a facile synthesis of highly substituted tetrahydro-1H-isoindolones from conjugated vinylic alkynes, imines, and ...

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

  Copper-Catalyzed Multicomponent Reaction: Synthesis of 4-Arylsulfonylimino-4,5-dihydrofuran Derivatives

  Yongjia Shang, Kai Ju, Xinwei He, Jinsong Hu, Shuyan Yu, Min Zhang, Kaisheng Liao, Lifen Wang and Ping Zhang
  The Journal of Organic Chemistry2010 75 (16), 5743-5745

  • Copper-Catalyzed Multicomponent Reaction: Synthesis of 4-Arylsulfonylimino-4,5-dihydrofuran Derivatives

    Yongjia Shang, Kai Ju, Xinwei He, Jinsong Hu, Shuyan Yu, Min Zhang, Kaisheng Liao, Lifen Wang and Ping Zhang
    The Journal of Organic Chemistry2010 75 (16), 5743-5745

    A series of 4-arylsulfonylimino-4,5-dihydrofurans (14 examples) were efficiently synthesized in good to excellent yields by using the copper-catalyzed three-component reaction between sulfonyl azides, phenylacetylene, and β-ketoesters in tetrahydrofuran (...

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

  The Development of Catalytic Nucleophilic Additions of Terminal Alkynes in Water

  Chao-Jun Li
  Accounts of Chemical Research2010 43 (4), 581-590

  • The Development of Catalytic Nucleophilic Additions of Terminal Alkynes in Water

    Chao-Jun Li
    Accounts of Chemical Research2010 43 (4), 581-590

    One of the major research endeavors in synthetic chemistry over the past two decades is the exploration of synthetic methods that work under ambient atmosphere with benign solvents, that maximize atom utilization, and that directly transform natural ...

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

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