Simple NMR predictors of catalytic hydrogenation activity for Rh(cod)Cl(NHC) complexes featuring fluorinated NHC ligands.

Alan Brisdon, Mohamad Shazwan Shah Jamil, Sultan Alkaabi

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    Abstract

    A series of imidazolium salts precursors for N-heterocyclic carbenes (NHCs) featuring fluoroaryl substituents have been prepared along with their selenides and rhodium complexes. Tests of the catalytic activity of the [Rh(cod)Cl(NHC)] complexes in the transfer hydrogenation of acetophenone with iPrOH shows that the activities of the rhodium complexes bearing fluorinated NHCs are better than their non-fluorinated counterparts. The order of activity being 4-F-C6H4 < 2,4-F2-C6H3 < 2,4,5-F3-C6H2 < 2,6-F2-C6H4 < 2,4,6-F3-C6H2. This order of reactivity is consistent with a number of simple NMR measures of the electronic properties of these systems, including 1JCH of the NHC.HBF4 salts, δ(77Se) of the NHC selenides and 1JRh-C and δ(13Ccarbene) of the [Rh(cod)Cl(NHC)] complexes.
    Original languageEnglish
    Pages (from-to)9317-9327
    Number of pages11
    JournalDalton Transactions
    Volume48
    Issue number25
    Early online date30 May 2019
    DOIs
    Publication statusPublished - 30 May 2019

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