Copper-Free Sonogashira Coupling Reaction with PdCl₂ in Water under Aerobic Conditions

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Abstract

A mild protocol for the copper-free Sonogashira coupling of aryl iodides with terminal acetylenes in water under aerobic conditions has been developed. The use of 1 mol % PdCl₂ in the presence of pyrrolidine allows the coupling reaction to proceed at room temperature or 50 °C with good to excellent yields.

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This article has been cited by 29 ACS Journal articles (5 most recent appear below).

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  Mechanistic Exploration of the Pd-Catalyzed Copper-Free Sonogashira Reaction

  Max García-Melchor, María C. Pacheco, Carmen Nájera, Agustí Lledós, and Gregori Ujaque
  ACS Catalysis2012 2 (1), 135-144

  • Mechanistic Exploration of the Pd-Catalyzed Copper-Free Sonogashira Reaction

    Max García-Melchor, María C. Pacheco, Carmen Nájera, Agustí Lledós, and Gregori Ujaque
    ACS Catalysis2012 2 (1), 135-144

    The reaction mechanism for the Pd-catalyzed Cu-free Sonogashira reaction is analyzed by means of density functional theory (DFT) calculations on a model system. The most common routes proposed in the literature for this reaction, namely, the ...

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

  Linear Polystyrene-Stabilized Palladium Nanoparticles-Catalyzed C–C Coupling Reaction in Water

  Atsushi Ohtaka, Takuto Teratani, Ryohei Fujii, Kanako Ikeshita, Takahiro Kawashima, Koichi Tatsumi, Osamu Shimomura, and Ryôki Nomura
  The Journal of Organic Chemistry2011 Article ASAP

  • Linear Polystyrene-Stabilized Palladium Nanoparticles-Catalyzed C–C Coupling Reaction in Water

    Atsushi Ohtaka, Takuto Teratani, Ryohei Fujii, Kanako Ikeshita, Takahiro Kawashima, Koichi Tatsumi, Osamu Shimomura, and Ryôki Nomura
    The Journal of Organic Chemistry2011 Article ASAP

    Linear polystyrene-stabilized PdO nanoparticles (PS-PdONPs) were prepared in water by thermal decomposition of Pd(OAc)2 in the presence of polystyrene. The immobilization degree of palladium was dependent on the molecular weight of polystyrene, while the ...

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

  Pd-Catalyzed Carbonylative Reactions of Aryl Iodides and Alkynyl Carboxylic Acids via Decarboxylative Couplings

  Ahbyeol Park, Kyungho Park, Yong Kim, and Sunwoo Lee
  Organic Letters2011 13 (5), 944-947

  • Pd-Catalyzed Carbonylative Reactions of Aryl Iodides and Alkynyl Carboxylic Acids via Decarboxylative Couplings

    Ahbyeol Park, Kyungho Park, Yong Kim, and Sunwoo Lee
    Organic Letters2011 13 (5), 944-947

    Alkynyl carboxylic acids reacted with aryl iodides under a CO atmosphere in the presence of a palladium catalyst to produce α,β-alkynyl aryl ketones in good yields. The maximum turnover number was 16 800. The desired carbonylative coupling was formed from ...

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

  Palladium-Catalyzed Cross-Coupling of Electron-Poor Terminal Alkynes with Arylboronic Acids under Ligand-Free and Aerobic Conditions

  Ming-Bo Zhou, Wen-Ting Wei, Ye-Xiang Xie, Yong Lei and Jin-Heng Li
  The Journal of Organic Chemistry2010 75 (16), 5635-5642

  • Palladium-Catalyzed Cross-Coupling of Electron-Poor Terminal Alkynes with Arylboronic Acids under Ligand-Free and Aerobic Conditions

    Ming-Bo Zhou, Wen-Ting Wei, Ye-Xiang Xie, Yong Lei and Jin-Heng Li
    The Journal of Organic Chemistry2010 75 (16), 5635-5642

    Palladium-catalyzed cross-coupling reaction of terminal alkynes with arylboronic acids has been described. In the presence of Pd(OAc)2 and Ag2O, a variety of terminal alkynes, including electron-poor terminal alkynes, smoothly underwent the reaction with ...

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

  Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Aryl Halides

  Jeongju Moon, Mihee Jang and Sunwoo Lee
  The Journal of Organic Chemistry2009 74 (3), 1403-1406

  • Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Aryl Halides

    Jeongju Moon, Mihee Jang and Sunwoo Lee
    The Journal of Organic Chemistry2009 74 (3), 1403-1406

    2-Octynoic acid and phenylpropiolic acid were employed for the palladium-catalyzed decarboxylative coupling reaction and with a variety of aryl halides. The former needed 1,4-bis(diphenylphosphino)butane (dppb) as a ligand and the latter tri-tert-...

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

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