N-methylacridinium salts: Carbon lewis acids in frustrated lewis pairs for σ-bond activation and catalytic reductions

Ewan R. Clark, Michael J. Ingleson

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    Abstract

    © 2014 Wiley-VCH Verlag GmbH & Co. KGaA.N-methylacridinium salts are Lewis acids with high hydride ion affinity but low oxophilicity. The cation forms a Lewis adduct with 4-(N,N-dimethylamino)pyridine but a frustrated Lewis pair (FLP) with the weaker base 2,6-lutidine which activates H2, even in the presence of H2O. Anion effects dominate reactivity, with both solubility and rate of H2cleavage showing marked anion dependency. With the optimal anion, a N-methylacridinium salt catalyzes the reductive transfer hydrogenation and hydrosilylation of aldimines through amine-boranes and silanes, respectively. Furthermore, the same salt is active for the catalytic dehydrosilylation of alcohols (primary, secondary, tertiary, and ArOH) by silanes with no observable over-reduction to the alkanes.
    Original languageEnglish
    Pages (from-to)11306-11309
    Number of pages3
    JournalAngewandte Chemie - International Edition
    Volume53
    Issue number42
    DOIs
    Publication statusPublished - 1 Oct 2014

    Keywords

    • Frustrated lewis pairs
    • Lewis acids
    • Reduction
    • Silanes
    • Synthetic methods

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