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Metal-free hydrogenation catalyzed by an air-stable borane: use of solvent as a frustrated Lewis base.

Scott DJ, Fuchter MJ, Ashley AE - Angew. Chem. Int. Ed. Engl. (2014)

Bottom Line: In recent years 'frustrated Lewis pairs' (FLPs) have been shown to be effective metal-free catalysts for the hydrogenation of many unsaturated substrates.This allows metal-free catalytic hydrogenations to be performed in donor solvent media under mild conditions; these systems are particularly effective for the hydrogenation of weakly basic substrates, including the first examples of metal-free catalytic hydrogenation of furan heterocycles.The air-stability of the most effective borane, B(C6Cl5)(C6F5)2, makes this a practically simple reaction method.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Imperial College London, London, SW7 2AZ (UK) http://www3.imperial.ac.uk/people/a.ashley.

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Proposed mechanisms for hydrogenation of imines by activation of H2 using either a) THF solvent or b) substrate as a frustrated Lewis base.
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fig05: Proposed mechanisms for hydrogenation of imines by activation of H2 using either a) THF solvent or b) substrate as a frustrated Lewis base.


Metal-free hydrogenation catalyzed by an air-stable borane: use of solvent as a frustrated Lewis base.

Scott DJ, Fuchter MJ, Ashley AE - Angew. Chem. Int. Ed. Engl. (2014)

Proposed mechanisms for hydrogenation of imines by activation of H2 using either a) THF solvent or b) substrate as a frustrated Lewis base.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4497615&req=5

fig05: Proposed mechanisms for hydrogenation of imines by activation of H2 using either a) THF solvent or b) substrate as a frustrated Lewis base.
Bottom Line: In recent years 'frustrated Lewis pairs' (FLPs) have been shown to be effective metal-free catalysts for the hydrogenation of many unsaturated substrates.This allows metal-free catalytic hydrogenations to be performed in donor solvent media under mild conditions; these systems are particularly effective for the hydrogenation of weakly basic substrates, including the first examples of metal-free catalytic hydrogenation of furan heterocycles.The air-stability of the most effective borane, B(C6Cl5)(C6F5)2, makes this a practically simple reaction method.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Imperial College London, London, SW7 2AZ (UK) http://www3.imperial.ac.uk/people/a.ashley.

Show MeSH
Related in: MedlinePlus