Issue 20, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
05 Dec 2012
Accepted
09 Jan 2013
First published
10 Jan 2013

Dalton Trans., 2013,42, 7373-7385

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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