"Imidazol(in)ium-2-carboxylates as N-Heterocyclic Carbene Ligand Precursors for Ruthenium Metathesis Initiators"

Xavier Sauvage, Albert Demonceau, and Lionel Delaude

journal cover 
          source: Macromolecular Symposia
            year: 2010
          volume: 293
      first page: 28
       last page: 32
             doi: 10.1002/masy.200900045

Abstract: Imidazol(in)ium-2-carboxylates were used as N-heterocyclic carbene (NHC) ligand precursors to convert the [RuCl2(p-cymene)]2 dimer into three ruthenium-arene complexes of the [RuCl2(p-cymene)(NHC)] type. The decarboxylation of NHC · CO2 betaines also provided a convenient synthetic path to prepare five well-known ruthenium-NHC catalysts for olefin metathesis and related reactions, including the second generation Grubbs and Hoveyda-Grubbs catalysts, via ligand exchange with phosphine-containing, first generation ruthenium-benzylidene or indenylidene complexes. Both procedures are particularly attractive from a practical point of view, because NHC · CO2 adducts are stable zwitterionic compounds that can be stored and handled with no particular precautions.

Keywords: Arene Ligands, Betaines, Organometallic Catalysts, Ring-Opening Metathesis Polymerization (ROMP), Zwitterions

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