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  • Title: N-donor functionalized N-heterocyclic carbene nickel(II) complexes in the Kumada coupling.
    Author: Berding J, van Dijkman TF, Lutz M, Spek AL, Bouwman E.
    Journal: Dalton Trans; 2009 Sep 21; (35):6948-55. PubMed ID: 20449135.
    Abstract:
    The synthesis and characterization of novel nickel(II) complexes bearing two bidentate N-heterocyclic carbene ligands functionalized with anionic N-donor moieties are described. Two different N-donor groups are employed, namely amido and benzimidazolato moieties. The solid-state structures of three of these complexes have been determined by X-ray crystallography. The amido-functionalized low-spin, square-planar Ni(II) complexes exhibit a cis geometry around the metal centre, while the benzimidazolato-functionalized complex crystallizes as the trans isomer. The activity of these novel complexes in the Kumada cross-coupling of phenylmagnesium chloride with 4-chloroanisole and 4-fluoroanisole was investigated. One of the benzimidazolato-functionalized complexes shows the highest activity in this reaction reported to date, yielding the desired product in quantitative yields within 30 min (4-chloroanisole), or 150 min (4-fluoroanisole) with only 1 mol% catalyst.
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