"Imidazol(in)ium-2-carboxylates as N-Heterocyclic Carbene Ligand Precursors for Suzuki-Miyaura Reactions"

Adriana Tudose, Lionel Delaude, Benoît André, and Albert Demonceau

journal cover 
          source: Tetrahedron Letters
            year: 2006
          volume: 47
      first page: 8529
       last page: 8533
             doi: 10.1016/j.tetlet.2006.09.139
graphical abstract

Abstract: Simple catalysts formed in situ from palladium acetate and a variety of imidazolium and imidazolinium carboxylates and dithiocarboxylates have been screened in the coupling of aryl halides with trans-2-phenylvinylboronic acid. Imidazol(in)ium carboxylates show an excellent activity, which compares to that displayed by the parent imidazol(in)ium chlorides, whereas imidazol(in)ium dithiocarboxylates are poorly efficient. Interestingly, the base employed exerts a profound influence on the trans/cis stereochemistry of the coupling product.

Keywords: Aryl Halides, Boronic Acids, Homogeneous Catalysis, N-Heterocyclic Carbene Ligands, Palladium and Compounds, Stilbenes, Suzuki-Miyaura Coupling Reactions

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