Metal-free hydrogenation catalyzed by an air-stable borane: use of solvent 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.Even so, limited functional-group tolerance restricts the range of solvents in which FLP-mediated reactions can be performed, with all FLP-mediated hydrogenations reported to date carried out in non-donor hydrocarbon or chlorinated solvents.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.
Affiliation: Department of Chemistry, Imperial College London, London, SW7 2AZ (UK) http://www3.imperial.ac.uk/people/a.ashley.Show MeSH
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Affiliation: Department of Chemistry, Imperial College London, London, SW7 2AZ (UK) http://www3.imperial.ac.uk/people/a.ashley.