N-Methylacridinium Salts: Carbon Lewis Acids in Frustrated Lewis Pairs for σ-Bond Activation and Catalytic Reductions

Ewan R. Clark, Michael J. Ingleson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

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 H2 cleavage 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 pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number42
DOIs
Publication statusPublished - 8 Oct 2014

Keywords

  • frustrated Lewis pairs
  • Lewis acids
  • reduction
  • silanes
  • synthetic methods

Fingerprint

Dive into the research topics of 'N-Methylacridinium Salts: Carbon Lewis Acids in Frustrated Lewis Pairs for σ-Bond Activation and Catalytic Reductions'. Together they form a unique fingerprint.

Cite this