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- Title
Carbon Halide Bond Activation of Aroyl Halides using an NHC-stabilized Nickel(0) Complex.
- Authors
Zell, Thomas; Radius, Udo
- Abstract
Aroyl complexes of the type trans-[Ni( iPr2Im)2(X)( C(O)Ar)] (X = Cl and Ar = Ph ( 2), 4- tBu-C6H4 ( 3) and C6F5 ( 4) and X = Br and Ar = Ph ( 5)) were prepared by oxidative addition reactions of carboxylic acid halides with the dinuclear nickel(0) complex [Ni2( iPr2Im)4(COD)] ( 1) ( iPr2Im = 1, 3-di isopropylimidazolin-2-ylidene; COD = 1, 5-cyclooctadien). The reported compounds were characterized by multinuclear NMR spectroscopy, EI-mass spectroscopy, IR spectroscopy, and elemental analysis. The benzoyl chloride complex trans-[Ni( iPr2Im)2(Cl)( C(O)Ph)] ( 2) as well as its bromide analogue trans-[Ni( iPr2Im)2(Br)( C(O)Ph)] ( 5) were additionally structurally characterized by single-crystal X-ray crystallography. NMR spectra of the crude products revealed the formation of minor amounts of the corresponding bis(halide) complexes trans-[Ni( iPr2Im)2(Cl)2] ( 6) and trans-[Ni( iPr2Im)2(Br)2] ( 7), depending on the aroyl halide used. Decarbonylation of the benzoyl complexes was observed upon irradiation of the complexes 2 and 5 with UV light. NMR analysis of the resulting mixtures of products revealed the formation of the phenyl halide complexes trans-[Ni( iPr2Im)2(Cl)(Ph)] ( 8) and [Ni( iPr2Im)2(Br)(Ph)] ( 9), as well as the formation of the bis(halide) complexes 6 and 7.
- Publication
Zeitschrift für Anorganische und Allgemeine Chemie, 2013, Vol 639, Issue 2, p334
- ISSN
0044-2313
- Publication type
Article
- DOI
10.1002/zaac.201200418