First Heck Reaction with Arenediazonium Cations with Recovery of Pd-Triolefinic Macrocyclic Catalyst

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Abstract

The air- and moisture-stable phosphine-free palladium(0) complex 1 is a highly active and recoverable catalyst for Heck olefination of aryl diazonium tetrafluoroborates. The reactions were performed under aerobic conditions at room temperature to give the coupling products in excellent yields.

Citing Articles

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This article has been cited by 17 ACS Journal articles (5 most recent appear below).

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  Influence of Electronically and Sterically Tunable Cinnamate Ligands on the Spectroscopic, Kinetic, and Thermodynamic Properties of Bis(triphenylphosphine)palladium(0) Olefin Complexes

  Magnus R. Buchner, Bettina Bechlars, Bernhard Wahl, and Klaus Ruhland
  Organometallics2012 31 (2), 588-601

  • Influence of Electronically and Sterically Tunable Cinnamate Ligands on the Spectroscopic, Kinetic, and Thermodynamic Properties of Bis(triphenylphosphine)palladium(0) Olefin Complexes

    Magnus R. Buchner, Bettina Bechlars, Bernhard Wahl, and Klaus Ruhland
    Organometallics2012 31 (2), 588-601

    A detailed study of the influence of electronic and steric characteristics of cinnamic acid esters on the spectroscopic, kinetic, and thermodynamic properties of bis(triphenylphosphine)palladium(0) cinnamic acid ester complexes is presented (51 different ...

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

  Observation of Binuclear Palladium Clusters upon ESI-MS Monitoring of the Suzuki–Miyaura Cross-Coupling Catalyzed by a Dichloro-bis(aminophosphine) Complex of Palladium

  Divya Agrawal, Detlef Schröder, and Christian M. Frech
  Organometallics2011 Article ASAP

  • Observation of Binuclear Palladium Clusters upon ESI-MS Monitoring of the Suzuki–Miyaura Cross-Coupling Catalyzed by a Dichloro-bis(aminophosphine) Complex of Palladium

    Divya Agrawal, Detlef Schröder, and Christian M. Frech
    Organometallics2011 Article ASAP

    Electrospray ionization mass spectrometry (ESI-MS) is used for monitoring the progress of the Suzuki–Miyaura cross-coupling reaction between bromobenzene and arylboronic acids using a palladium dichloro-bis(aminophosphine) complex as a precatalyst. The ...

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

  Pd-Catalyzed Arylation Reactions with Phenol Diazonium Salts: Application in the Synthesis of Diarylheptanoids

  Bernd Schmidt, Frank Hölter, Alexandra Kelling, and Uwe Schilde
  The Journal of Organic Chemistry2011 Article ASAP

  • Pd-Catalyzed Arylation Reactions with Phenol Diazonium Salts: Application in the Synthesis of Diarylheptanoids

    Bernd Schmidt, Frank Hölter, Alexandra Kelling, and Uwe Schilde
    The Journal of Organic Chemistry2011 Article ASAP

    The first total synthesis of the natural product (3S,7R)-5,6-dehydro-de-O-methyl centrolobine and various analogues is reported, using a highly regio- and diastereoselective Mizoroki−Heck reaction of phenol diazonium salts and enantiopure dihydropyrans. ...

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

  Insight into Solution Chemistry from Gas-Phase Experiments

  Divya Agrawal and Detlef Schröder
  Organometallics2011 30 (1), 32-35

  • Insight into Solution Chemistry from Gas-Phase Experiments

    Divya Agrawal and Detlef Schröder
    Organometallics2011 30 (1), 32-35
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Sequential One-Pot Combination of Multireactions through Multicatalysis: A General Approach to Rapid Assembly of Functionalized Push−Pull Olefins, Phenols, and 2-Methyl-2H-chromenes

  Dhevalapally B. Ramachary, Kinthada Ramakumar, Adluri Bharanishashank, and Vidadala V. Narayana
  Journal of Combinatorial Chemistry2010 12 (6), 855-876

  • Sequential One-Pot Combination of Multireactions through Multicatalysis: A General Approach to Rapid Assembly of Functionalized Push−Pull Olefins, Phenols, and 2-Methyl-2H-chromenes

    Dhevalapally B. Ramachary, Kinthada Ramakumar, Adluri Bharanishashank, and Vidadala V. Narayana
    Journal of Combinatorial Chemistry2010 12 (6), 855-876

    A general, sustainable and practical process for the sequential cascade one-pot synthesis of library of highly substituted push−pull olefins, phenols and 2-methyl-2H-chromenes was reported through multicatalysis cascade (MCC) reactions. Direct sequential ...

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

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