Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 42, Pages 11306-11309Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406122
Keywords
frustrated Lewis pairs; Lewis acids; reduction; silanes; synthetic methods
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Funding
- Leverhulme Trust (ERC)
- Royal Society
- EPSRC [EP/K039547/1]
- EPSRC [EP/K039547/1, EP/J003921/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/J003921/1, EP/K039547/1] Funding Source: researchfish
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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 H-2, even in the presence of H2O. Anion effects dominate reactivity, with both solubility and rate of H-2 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.
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