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Issue 20, 2013
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Anionic and zwitterionic copper(I) complexes incorporating an anionic N-heterocyclic carbene decorated with a malonate backbone: synthesis, structure and catalytic applications

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Abstract

The anionic malonate-derived N-heterocyclic carbenes (maloNHCs) react cleanly and rapidly with copper chloride to generate the anionic complexes of type [(maloNHC)CuCl]·Li, which crystallize in the solid state either in an oligomeric trimer arrangement or in polymeric helixes depending on the substitution pattern and the solvent. Ten zwitterionic heteroleptic Cu(I) complexes combining the anionic maloNHC and a neutral imidazol-2-ylidene are also obtained in a very selective manner and fully characterized. Whereas the anionic complexes are relatively active catalysts for the hydrosilylation of carbonyl compounds, the zwitterionic complexes reveal to be efficient and extremely robust pre-catalysts for the intramolecular cyclopropanation reaction of a diazo ester and outperform the corresponding cationic Cu(I) complexes with classical imidazol-2-ylidenes.

Graphical abstract: Anionic and zwitterionic copper(i) complexes incorporating an anionic N-heterocyclic carbene decorated with a malonate backbone: synthesis, structure and catalytic applications

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Publication details

The article was received on 05 Dec 2012, accepted on 09 Jan 2013 and first published on 10 Jan 2013


Article type: Paper
DOI: 10.1039/C3DT32919D
Citation: Dalton Trans., 2013,42, 7373-7385
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    Anionic and zwitterionic copper(I) complexes incorporating an anionic N-heterocyclic carbene decorated with a malonate backbone: synthesis, structure and catalytic applications

    V. César, C. Barthes, Y. C. Farré, S. V. Cuisiat, B. Y. Vacher, R. Brousses, N. Lugan and G. Lavigne, Dalton Trans., 2013, 42, 7373
    DOI: 10.1039/C3DT32919D

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