Sonogashira Coupling Reaction with Diminished Homocoupling

• Abstract
• Full Text HTML
• Hi-Res PDF[62 KB]
• PDF w/ Links[135 KB]

• Supporting Info
• Figures
• Citing Articles

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

• PDF/HTML,
  figures/images,
  references and tables,
  (where available)

Abstract

The side product from homocoupling reaction of two terminal acetylenes in the Sonogashira reaction can be reduced to about 2% using an atmosphere of hydrogen gas diluted with nitrogen or argon. Terminal arylethynes, diarylethynes, and a few new arylpyridylethynes with donor substituents have been synthesized in very good yields. Comparative control experiments suggest that the homocoupling yield is determined by concentration of both catalyst and oxygen.

Citing Articles

View all 106 citing articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

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

• 

  A Multitechnique Physicochemical Investigation of Various Factors Controlling the Photoaction Spectra and of Some Aspects of the Electron Transfer for a Series of Push–Pull Zn(II) Porphyrins Acting as Dyes in DSSCs

  Alessio Orbelli Biroli, Francesca Tessore, Maddalena Pizzotti, Cinzia Biaggi, Renato Ugo, Stefano Caramori, Alessandro Aliprandi, Carlo Alberto Bignozzi, Filippo De Angelis, Giacomo Giorgi, Emanuela Licandro, and Elena Longhi
  The Journal of Physical Chemistry C2011 115 (46), 23170-23182

  • A Multitechnique Physicochemical Investigation of Various Factors Controlling the Photoaction Spectra and of Some Aspects of the Electron Transfer for a Series of Push–Pull Zn(II) Porphyrins Acting as Dyes in DSSCs

    Alessio Orbelli Biroli, Francesca Tessore, Maddalena Pizzotti, Cinzia Biaggi, Renato Ugo, Stefano Caramori, Alessandro Aliprandi, Carlo Alberto Bignozzi, Filippo De Angelis, Giacomo Giorgi, Emanuela Licandro, and Elena Longhi
    The Journal of Physical Chemistry C2011 115 (46), 23170-23182

    A multitechnique physicochemical comparative investigation involving TDDFT theoretical calculations, steady-state and time-resolved electronic absorption spectra, and electrochemical and photoelectrochemical investigations was carried out on a family of ...

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

  Toward a Four-Toothed Molecular Bevel Gear with C₂-Symmetrical Rotors

  Chen-Yi Kao, Ya-Ting Hsu, Hsiu-Feng Lu, Ito Chao, Shou-Ling Huang, Ying-Chih Lin, Wei-Ting Sun, and Jye-Shane Yang
  The Journal of Organic Chemistry2011 Article ASAP

  • Toward a Four-Toothed Molecular Bevel Gear with C₂-Symmetrical Rotors

    Chen-Yi Kao, Ya-Ting Hsu, Hsiu-Feng Lu, Ito Chao, Shou-Ling Huang, Ying-Chih Lin, Wei-Ting Sun, and Jye-Shane Yang
    The Journal of Organic Chemistry2011 Article ASAP

    The design, synthesis, conformational analysis, and variable-temperature NMR studies of pentiptycene-based molecular gears Pp2X, where Pp is the unlabeled (in 1H) or methoxy groups-labeled (in 1OM) pentiptycene rotor and X is the phenylene stator ...

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

  Click-Reagent Version of Sonogashira Coupling Protocol to Conjugated Fluorescent Alkynes with No or Reduced Homocoupling

  Subhendu Sekhar Bag, Rajen Kundu, and Manas Das
  The Journal of Organic Chemistry2011 76 (7), 2332-2337

  • Click-Reagent Version of Sonogashira Coupling Protocol to Conjugated Fluorescent Alkynes with No or Reduced Homocoupling

    Subhendu Sekhar Bag, Rajen Kundu, and Manas Das
    The Journal of Organic Chemistry2011 76 (7), 2332-2337

    A click-reagent version of the Sonogashira-coupling protocol has been developed. Diarylalkynes with donor and/or acceptor substituents have been synthesized via this protocol at moderate to excellent yields and with no or drastically reduced quantities of ...

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

  Phthalocyanine-Peptide Conjugates via Palladium-Catalyzed Cross-Coupling Reactions

  Hasrat Ali, Samia Ait-Mohand, Simon Gosselin, Johan E. van Lier, and Brigitte Guérin
  The Journal of Organic Chemistry2011 76 (6), 1887-1890

  • Phthalocyanine-Peptide Conjugates via Palladium-Catalyzed Cross-Coupling Reactions

    Hasrat Ali, Samia Ait-Mohand, Simon Gosselin, Johan E. van Lier, and Brigitte Guérin
    The Journal of Organic Chemistry2011 76 (6), 1887-1890

    Phthalocyanines (Pc) were conjugated with peptide moieties to improve their target selectivity for potential use as fluorescence and/or positron emission tomography (PET) probes in medical imaging. Three synthetic methods based on palladium-catalyzed ...

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

  Reactive Iron Carbonyl Reagents via Reaction of Metal Alkoxides with Fe(CO)₅ or Fe₂(CO)₉: Synthesis of Cyclobutenediones via Double Carbonylation of Alkynes

  Mallesh Beesu and Mariappan Periasamy
  The Journal of Organic Chemistry2011 76 (2), 543-549

  • Reactive Iron Carbonyl Reagents via Reaction of Metal Alkoxides with Fe(CO)₅ or Fe₂(CO)₉: Synthesis of Cyclobutenediones via Double Carbonylation of Alkynes

    Mallesh Beesu and Mariappan Periasamy
    The Journal of Organic Chemistry2011 76 (2), 543-549

    Alkoxy bases such as t-BuOK react with Fe(CO)5 to give reactive iron carbonyl intermediates that in turn react with alkynes at 70 °C in THF to give 1,2-cyclobutenediones in 70−93% yields after CuCl2·2H2O oxidation. A novel 1,2-diacyloxyferrole derivative ...

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

SciFinder Links

• Get Reference Detail
• Get Substances
• Get Reactions
• Get Cited
• Get Citing