Zinc Chloride-Promoted Aryl Bromide−Alkyne Cross-Coupling Reactions at Room Temperature

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Abstract

Substoichiometric amounts of ZnCl₂ promote the room temperature, Pd/P(t-Bu)₃-catalyzed cross-coupling of aryl bromides with alkynes. Pd(I) dimer 1 is demonstrated to be a particularly active precatalyst for this reaction. The reaction is general for a wide variety of aryl bromides.

Citing Articles

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

• 

  Preparation of Shape-Persistent Macrocycles with a Single Pyridine Unit by Double Cross-Coupling Reactions of Aryl Bromides and Alkynes

  Ryu Yamasaki, Atsushi Shigeto, and Shinichi Saito
  The Journal of Organic Chemistry2011 76 (24), 10299-10305

  • Preparation of Shape-Persistent Macrocycles with a Single Pyridine Unit by Double Cross-Coupling Reactions of Aryl Bromides and Alkynes

    Ryu Yamasaki, Atsushi Shigeto, and Shinichi Saito
    The Journal of Organic Chemistry2011 76 (24), 10299-10305

    A double Sonogashira-type coupling reaction between aryl bromides and alkynes using a catalytic Pd/XPhos (2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl) system was introduced as an efficient method for the synthesis of shape-persistent macrocycles ...

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

  Finding Use of Palladium(I) Dimer/Methylalumoxane Catalysts in Norbornene Polymerization

  Ling Zhang, Mian Zhang, and Qing Wu
  Organometallics2010 29 (22), 5766-5768

  • Finding Use of Palladium(I) Dimer/Methylalumoxane Catalysts in Norbornene Polymerization

    Ling Zhang, Mian Zhang, and Qing Wu
    Organometallics2010 29 (22), 5766-5768
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Synthesis and X-ray Structure Determination of Highly Active Pd(II), Pd(I), and Pd(0) Complexes of Di(tert-butyl)neopentylphosphine (DTBNpP) in the Arylation of Amines and Ketones

  Lensey L. Hill, Jason L. Crowell, Strudwick L. Tutwiler, Nicholas L. Massie, C. Corey Hines, Scott T. Griffin, Robin D. Rogers, and Kevin H. Shaughnessy, Gabriela A. Grasa, Carin C. C. Johansson Seechurn, Hongbo Li, and Thomas J. Colacot , Joe Chou and Christopher J. Woltermann
  The Journal of Organic Chemistry2010 75 (19), 6477-6488

  • Synthesis and X-ray Structure Determination of Highly Active Pd(II), Pd(I), and Pd(0) Complexes of Di(tert-butyl)neopentylphosphine (DTBNpP) in the Arylation of Amines and Ketones

    Lensey L. Hill, Jason L. Crowell, Strudwick L. Tutwiler, Nicholas L. Massie, C. Corey Hines, Scott T. Griffin, Robin D. Rogers, and Kevin H. Shaughnessy, Gabriela A. Grasa, Carin C. C. Johansson Seechurn, Hongbo Li, and Thomas J. Colacot , Joe Chou and Christopher J. Woltermann
    The Journal of Organic Chemistry2010 75 (19), 6477-6488

    The air-stable complex Pd(η3-allyl)(DTBNpP)Cl (DTBNpP = di(tert-butyl)neopentylphosphine) serves as a highly efficient precatalyst for the arylation of amines and enolates using aryl bromides and chlorides under mild conditions with yields ranging from 74%...

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

  A Rapid and Efficient Sonogashira Protocol and Improved Synthesis of Free Fatty Acid 1 (FFA1) Receptor Agonists

  Elisabeth Christiansen, Maria E. Due-Hansen and Trond Ulven
  The Journal of Organic Chemistry2010 75 (4), 1301-1304

  • A Rapid and Efficient Sonogashira Protocol and Improved Synthesis of Free Fatty Acid 1 (FFA1) Receptor Agonists

    Elisabeth Christiansen, Maria E. Due-Hansen and Trond Ulven
    The Journal of Organic Chemistry2010 75 (4), 1301-1304

    A protocol for rapid and efficient Pd/Cu-catalyzed coupling of aryl bromides and iodides to terminal alkynes has been developed with use of 2-(di-tert-butylphosphino)-N-phenylindole (cataCXium PIntB) as ligand in TMEDA and water. The new protocol ...

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

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