Pd(quinoline-8-carboxylate)₂ as a Low-Priced, Phosphine-Free Catalyst for Heck and Suzuki Reactions

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Abstract

N,O-Bidentate compounds were systematically evaluated as phosphine-free ligands for Pd-catalyzed C−C bond-formation reactions through kinetic measurements. Pd(quinoline-8-carboxylate)₂ was identified as one of the most efficient, yet still low-priced, phosphine-free catalysts for Heck as well as Suzuki reactions of unactivated aryl bromides with high turnover numbers up to ca. 10,000.

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

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  Charge-Tagged Acetate Ligands As Mass Spectrometry Probes for Metal Complexes Investigations: Applications in Suzuki and Heck Phosphine-Free Reactions

  Felipe F. D. Oliveira, Marcelo R. dos Santos, Priscila M. Lalli, Eduardo M. Schmidt, Peter Bakuzis, Alexandre A. M. Lapis, Adriano L. Monteiro, Marcos N. Eberlin, and Brenno A. D. Neto
  The Journal of Organic Chemistry2011 76 (24), 10140-10147

  • Charge-Tagged Acetate Ligands As Mass Spectrometry Probes for Metal Complexes Investigations: Applications in Suzuki and Heck Phosphine-Free Reactions

    Felipe F. D. Oliveira, Marcelo R. dos Santos, Priscila M. Lalli, Eduardo M. Schmidt, Peter Bakuzis, Alexandre A. M. Lapis, Adriano L. Monteiro, Marcos N. Eberlin, and Brenno A. D. Neto
    The Journal of Organic Chemistry2011 76 (24), 10140-10147

    An acetate anion bearing an imidazolium cation as its charge tag was reacted with M(OAc)2 complexes (where M = Ni, Cu, and Pd; in situ reaction) to form members of a new class of charge-tagged metal complexes. The formation of these unprecedented ...

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

  Palladium-Catalyzed Heck Reaction of Aryl Chlorides under Mild Conditions Promoted by Organic Ionic Bases

  Hua-Jian Xu, Yong-Qiang Zhao, and Xin-Feng Zhou
  The Journal of Organic Chemistry2011 76 (19), 8036-8041

  • Palladium-Catalyzed Heck Reaction of Aryl Chlorides under Mild Conditions Promoted by Organic Ionic Bases

    Hua-Jian Xu, Yong-Qiang Zhao, and Xin-Feng Zhou
    The Journal of Organic Chemistry2011 76 (19), 8036-8041

    An efficient Pd-catalyzed Heck reaction of aryl chlorides with olefins under mild conditions is described. High yields of products were achieved with n-Bu4N+OAc– as base. Significantly, the temperature of the Heck reaction of diverse nonactivated aryl ...

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

  Trifunctional N,N,O-Terdentate Amido/Pyridyl Carboxylate Ligated Pd(II) Complexes for Heck and Suzuki Reactions

  M. Lakshmi Kantam, P. Srinivas, Jagjit Yadav, Pravin R. Likhar and Suresh Bhargava
  The Journal of Organic Chemistry2009 74 (13), 4882-4885

  • Trifunctional N,N,O-Terdentate Amido/Pyridyl Carboxylate Ligated Pd(II) Complexes for Heck and Suzuki Reactions

    M. Lakshmi Kantam, P. Srinivas, Jagjit Yadav, Pravin R. Likhar and Suresh Bhargava
    The Journal of Organic Chemistry2009 74 (13), 4882-4885

    Trifunctional N,N,O-terdentate amido/pyridyl carboxylate Pd(II) complexes were highly active and stable phosphine-free catalysts for Heck and room-temperature Suzuki reactions with high turnover numbers up to ca. 104.

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

  Facile and Efficient Olefination of Aryl Halides Catalyzed by a Palladium Complex Containing a Heteroarene-Functionalized N-Heterocyclic Carbene

  Xiaoming Zhang, Zhenxing Xi, Ailing Liu and Wanzhi Chen
  Organometallics2008 27 (17), 4401-4406

  • Facile and Efficient Olefination of Aryl Halides Catalyzed by a Palladium Complex Containing a Heteroarene-Functionalized N-Heterocyclic Carbene

    Xiaoming Zhang, Zhenxing Xi, Ailing Liu and Wanzhi Chen
    Organometallics2008 27 (17), 4401-4406

    [Ag4(L)4](PF6)4 and [Pd(L)2](PF6)2 (L = 3-(2,4-dimethyl-1,8-naphthyrid-7-yl)-1-picolylimidazolylidene) have been prepared and fully characterized. The palladium complex, containing unsymmetric heteroarene-functionalized N-heterocyclic carbenes, has proven ...

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

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