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Direct Arylation of Heteroaromatic Compounds with Congested, Functionalised Aryl Bromides at Low Palladium/Triphosphane Catalyst Loading

Authors

  • David Roy,

    1. UMR-CNRS 6226, équipe “Catalyse et Organométalliques”, Université de Rennes I, Campus de Beaulieu, 35042 Rennes (France), Fax: (+33) 2-23-23-63-84
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  • Sophal Mom,

    1. UMR-CNRS 5260 - Institut de Chimie Moléculaire, Université de Bourgogne, 9 avenue Alain Savary, 21078 Dijon (France), Fax: (+33) 3-80-39-36-82
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  • Prof. Dr. Dominique Lucas,

    1. UMR-CNRS 5260 - Institut de Chimie Moléculaire, Université de Bourgogne, 9 avenue Alain Savary, 21078 Dijon (France), Fax: (+33) 3-80-39-36-82
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  • Dr. Hélène Cattey,

    1. UMR-CNRS 5260 - Institut de Chimie Moléculaire, Université de Bourgogne, 9 avenue Alain Savary, 21078 Dijon (France), Fax: (+33) 3-80-39-36-82
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  • Prof. Dr. Jean-Cyrille Hierso,

    Corresponding author
    1. UMR-CNRS 5260 - Institut de Chimie Moléculaire, Université de Bourgogne, 9 avenue Alain Savary, 21078 Dijon (France), Fax: (+33) 3-80-39-36-82
    • UMR-CNRS 5260 - Institut de Chimie Moléculaire, Université de Bourgogne, 9 avenue Alain Savary, 21078 Dijon (France), Fax: (+33) 3-80-39-36-82
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  • Dr. Henri Doucet

    Corresponding author
    1. UMR-CNRS 6226, équipe “Catalyse et Organométalliques”, Université de Rennes I, Campus de Beaulieu, 35042 Rennes (France), Fax: (+33) 2-23-23-63-84
    • UMR-CNRS 6226, équipe “Catalyse et Organométalliques”, Université de Rennes I, Campus de Beaulieu, 35042 Rennes (France), Fax: (+33) 2-23-23-63-84
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Abstract

A new ferrocenyl triphosphane ligand associated to palladium was found to be an efficient catalyst for the direct coupling of highly congested, functionalised aryl bromides with a variety of heteroarenes. These coupling reactions can generally be performed by using a low-loading (0.1–0.5 mol %) of the catalyst. The present protocol tolerates important and useful functional groups, which allows for further elaboration into more sophisticated heterocyclic molecules. The straightforward arylation of heteroaromatic compounds with congested ortho-substituted aryl bromides may permit further convergent syntheses of diverse ligands, biologically active molecules and molecular materials in only a few steps.

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