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

Clark, Ewan R., Ingleson, Michael J. (2014) N-Methylacridinium Salts: Carbon Lewis Acids in Frustrated Lewis Pairs for ?-Bond Activation and Catalytic Reductions. Angewandte Chemie International Edition, 53 (42). pp. 11306-11309. ISSN 1433-7851. (doi:10.1002/anie.201406122)

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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.

Item Type: Article
DOI/Identification number: 10.1002/anie.201406122
Uncontrolled keywords: Frustrated lewis pairs, Lewis acids, Reduction, Silanes, Synthetic methods, Functional Materials Group
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Sciences > School of Physical Sciences > Functional Materials Group
Depositing User: Giles Tarver
Date Deposited: 29 Jul 2015 15:08 UTC
Last Modified: 10 Feb 2020 10:16 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/49871 (The current URI for this page, for reference purposes)
Clark, Ewan R.: https://orcid.org/0000-0001-7287-2631
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