Efficient Stille Cross-Coupling Reaction Catalyzed by the Pd(OAc)₂/Dabco Catalytic System

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Abstract

An efficient Pd(OAc)₂/Dabco-catalyzed Stille cross-coupling reaction procedure has been developed. In the presence of Pd(OAc)₂ and Dabco (triethylenediamine), various aryl halides including aryl iodides, aryl bromides, and activated aryl chlorides were coupled efficiently with organotin compounds to afford the corresponding biaryls, alkene, and alkynes in good to excellent yields. Furthermore, high TONs [turnover numbers, up to 980 000 TONs for the coupling reaction of 1-bromo-4-nitrobenzene and furan-2-yltributyltin] for the Stille cross-coupling reaction were observed.

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This article has been cited by 11 ACS Journal articles (5 most recent appear below).

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  Hiyama Cross-Coupling of Arenediazonium Salts under Mild Reaction Conditions

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  The Journal of Organic Chemistry2011 76 (22), 9261-9268

  • Hiyama Cross-Coupling of Arenediazonium Salts under Mild Reaction Conditions

    Kai Cheng, Chen Wang, Yiyuan Ding, Qingbao Song, Chenze Qi, and Xian-Man Zhang
    The Journal of Organic Chemistry2011 76 (22), 9261-9268

    Palladium acetate [Pd(OAc)2]-catalyzed Hiyama cross-coupling of arenediazonium salts with organosilanes was found to generate biaryl products in high yields in alcoholic solutions. The simple and efficient protocol does not require any bases, ligands, or ...

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

  Pd(PPh₃)₄-PEG 400 Catalyzed Protocol for the Atom-Efficient Stille Cross-Coupling Reaction of Organotin with Aryl Bromides

  Wen-Jun Zhou, Ke-Hu Wang and Jin-Xian Wang
  The Journal of Organic Chemistry2009 74 (15), 5599-5602

  • Pd(PPh₃)₄-PEG 400 Catalyzed Protocol for the Atom-Efficient Stille Cross-Coupling Reaction of Organotin with Aryl Bromides

    Wen-Jun Zhou, Ke-Hu Wang and Jin-Xian Wang
    The Journal of Organic Chemistry2009 74 (15), 5599-5602

    Aryl bromides (4 equiv) were coupled efficiently with organotin (1 equiv) in an atom-efficient way using the tetra(triphenylphosphine)palladium/polyethylene glycol 400 (Pd(PPh3)4/PEG 400) catalytic system in the presence of sodium acetate (NaOAc) as base ...

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

  Palladium-Catalyzed Intramolecular Reactions of (E)-2,2-Disubstituted 1-Alkenyldimethylalanes with Aryl Triflates

  Eric Fillion, Vincent É. Trépanier, Jarkko J. Heikkinen, Anna A. Remorova, Rebekah J. Carson, Julie M. Goll and Adam Seed
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  • Palladium-Catalyzed Intramolecular Reactions of (E)-2,2-Disubstituted 1-Alkenyldimethylalanes with Aryl Triflates

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    Organometallics2009 28 (12), 3518-3531

    A stereospecific synthesis of sp3-gem-dimetallic palladio(II) dialkylaluminoalkane species via the intramolecular Pd-catalyzed arylation of (E)-2,2-disubstituted 1-alkenyldimethylalanes with aryl triflates is reported. In the presence of DABCO, these ...

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

  Utilization of Sequential Palladium-Catalyzed Cross-Coupling Reactions in the Stereospecific Synthesis of Trisubstituted Olefins

  Ioannis N. Houpis, Didier Shilds, Ulrike Nettekoven, Anita Schnyder, Erhart Bappert, Koen Weerts, Martine Canters and Wim Vermuelen
  Organic Process Research & Development2009 13 (3), 598-606

  • Utilization of Sequential Palladium-Catalyzed Cross-Coupling Reactions in the Stereospecific Synthesis of Trisubstituted Olefins

    Ioannis N. Houpis, Didier Shilds, Ulrike Nettekoven, Anita Schnyder, Erhart Bappert, Koen Weerts, Martine Canters and Wim Vermuelen
    Organic Process Research & Development2009 13 (3), 598-606

    A stereospecific synthesis of the drug-candidate 1 is described. The synthetic sequence, aimed at accomplishing modularity and cost savings, features a series of organometallic steps to afford stereospecifically the desired trisubstituded olefin active ...

    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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