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Issue 11, 2015
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A T-shaped Ni[κ2-(CF2)4–] NHC complex: unusual Csp3–F and M–CF bond functionalization reactions

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Abstract

A T-shaped octafluoronickelacyclopentane–NHC complex is prepared and characterized. While the solid-state structure includes a weak isopropyl-CH3 agostic interaction, the reactivity of this complex with Lewis- and Brønsted acids is clearly enhanced by its low coordination number. Reaction with Me3SiOTf, for example, yielded a rare metal–heptafluorocyclobutyl complex whereas carboxylic acids gave substitution at the α-carbon and/or Ni–CF bond protonolysis to afford thermally robust 4H-octafluorobutyl Ni complexes.

Graphical abstract: A T-shaped Ni[κ2-(CF2)4–] NHC complex: unusual Csp3–F and M–CF bond functionalization reactions

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Publication details

The article was received on 25 May 2015, accepted on 27 Jul 2015 and first published on 06 Aug 2015


Article type: Edge Article
DOI: 10.1039/C5SC01886B
Citation: Chem. Sci., 2015,6, 6392-6397
  • Open access: Creative Commons BY-NC license
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    A T-shaped Ni[κ2-(CF2)4–] NHC complex: unusual Csp3–F and M–CF bond functionalization reactions

    N. O. Andrella, A. J. Sicard, S. I. Gorelsky, I. Korobkov and R. T. Baker, Chem. Sci., 2015, 6, 6392
    DOI: 10.1039/C5SC01886B

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