Ruthenium(II)-catalysed Functionalisation of C[BOND]H Bonds via a Six-membered Cyclometallate: Monoarylation of Aryl 2-pyridyl Ketones

Authors

  • Bin Li,

    1. UMR 6226 CNRS-Université de Rennes, Institut des Sciences Chimiques de Rennes, Team - Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042, Rennes (France), Fax: (+33) 2-23-23-69-39
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  • Prof. Dr. Christophe Darcel,

    Corresponding author
    1. UMR 6226 CNRS-Université de Rennes, Institut des Sciences Chimiques de Rennes, Team - Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042, Rennes (France), Fax: (+33) 2-23-23-69-39
    • UMR 6226 CNRS-Université de Rennes, Institut des Sciences Chimiques de Rennes, Team - Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042, Rennes (France), Fax: (+33) 2-23-23-69-39

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  • Prof. Dr. Pierre H. Dixneuf

    Corresponding author
    1. UMR 6226 CNRS-Université de Rennes, Institut des Sciences Chimiques de Rennes, Team - Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042, Rennes (France), Fax: (+33) 2-23-23-69-39
    • UMR 6226 CNRS-Université de Rennes, Institut des Sciences Chimiques de Rennes, Team - Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042, Rennes (France), Fax: (+33) 2-23-23-69-39

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Abstract

Selective monoarylation of aryl 2-pyridyl ketones with a variety of arylbromides via arene sp2 C[BOND]H bond activation/functionalisation is achieved with a [RuCl2(p-cymene)]2/ p-CF3C6H4CO2H catalytic system. The reaction via a 6-membered ruthenacycle is more difficult to perform than via a 5-membered cyclometallate but the activation of only one ortho C[BOND]H bond is unprecedentedly highly selective. A variety of functional 2-pyridine derivatives are easily obtained. It is shown via H/D exchange that the carboxylic acid favours the reversible C[BOND]H bond activation.

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