Copper-Catalyzed Synthesis of 1,3-Enynes

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Abstract

We report a copper(I)-catalyzed procedure for the synthesis of 1,3-enynes. This method affords a variety of enynes in good to excellent yields. This method can tolerate a variety of functional groups, does not require the use of expensive additives, and is palladium-free.

Citing Articles

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This article has been cited by 13 ACS Journal articles (5 most recent appear below).

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  Copper-Catalyzed Amination of Alkenyl Halides: Efficient Method for the Synthesis of Enamines

  Yuxing Wang, Qian Liao and Chanjuan Xi
  Organic Letters2010 12 (13), 2951-2953

  • Copper-Catalyzed Amination of Alkenyl Halides: Efficient Method for the Synthesis of Enamines

    Yuxing Wang, Qian Liao and Chanjuan Xi
    Organic Letters2010 12 (13), 2951-2953

    A copper-catalyzed method for the coupling of alkenyl halides with secondary amines has been developed. This protocol used a combination of 10 mol % copper iodide and 20 mol % N,N′-dimethylethane-1,2-diamine as catalyst. The reaction proceeded with ...

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

  Sonogashira Reactions with Propyne: Facile Synthesis of 4-Hydroxy-2-methylbenzofurans from Iodoresorcinols

  Martin A. Berliner, Eric M. Cordi, Joshua R. Dunetz and Kristin E. Price
  Organic Process Research & Development2010 14 (1), 180-187

  • Sonogashira Reactions with Propyne: Facile Synthesis of 4-Hydroxy-2-methylbenzofurans from Iodoresorcinols

    Martin A. Berliner, Eric M. Cordi, Joshua R. Dunetz and Kristin E. Price
    Organic Process Research & Development2010 14 (1), 180-187

    The Sonogashira reaction of terminal alkynes and ortho-halophenols with subsequent cyclization is a well-precedented method for the synthesis of substituted benzofurans. Here we describe the extension of this method to the coupling of 2-iodoresorcinols ...

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

  CuI Nanoparticles for C−N and C−O Cross Coupling of Heterocyclic Amines and Phenols with Chlorobenzenes

  B. Sreedhar, R. Arundhathi, P. Linga Reddy and M. Lakshmi Kantam
  The Journal of Organic Chemistry2009 74 (20), 7951-7954

  • CuI Nanoparticles for C−N and C−O Cross Coupling of Heterocyclic Amines and Phenols with Chlorobenzenes

    B. Sreedhar, R. Arundhathi, P. Linga Reddy and M. Lakshmi Kantam
    The Journal of Organic Chemistry2009 74 (20), 7951-7954

    Employing CuI nanoparticles as an efficient catalyst for the cross-coupling reactions of various N/O nucleophilic reagents with aryl chlorides could be successfully carried out under mild conditions in the absence of both the ligands and strong bases. A ...

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

  Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis

  Gwilherm Evano, Nicolas Blanchard and Mathieu Toumi
  Chemical Reviews2008 108 (8), 3054-3131

  • Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis

    Gwilherm Evano, Nicolas Blanchard and Mathieu Toumi
    Chemical Reviews2008 108 (8), 3054-3131
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Hydroxyapatite-Supported Palladium-Catalyzed Efficient Synthesis of (E)-2-Alkene-4-ynecarboxylic Esters. Intense Fluorescene Emission of Selected Compounds

  Brindaban C. Ranu, Laksmikanta Adak and Kalicharan Chattopadhyay
  The Journal of Organic Chemistry2008 73 (14), 5609-5612

  • Hydroxyapatite-Supported Palladium-Catalyzed Efficient Synthesis of (E)-2-Alkene-4-ynecarboxylic Esters. Intense Fluorescene Emission of Selected Compounds

    Brindaban C. Ranu, Laksmikanta Adak and Kalicharan Chattopadhyay
    The Journal of Organic Chemistry2008 73 (14), 5609-5612

    A simple procedure for the synthesis of substituted (E)-2-alkene-4-ynecarboxylic esters has been achieved using hydroxyapatite-supported palladium as efficient catalyst surface. The catalyst is recycled, and the turnover number (TON) based on Pd is ...

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

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