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Hydrogenations without hydrogen: titania photocatalyzed reductions of maleimides and aldehydes

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Author(s)

David W. Manley, Luca Buzzetti, Andrew MacKessack-Leitch, John C. Walton

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Abstract

A mild procedure for the reduction of electron-deficient alkenes and carbonyl compounds is described. UVA irradiations of substituted maleimides with dispersions of titania (Aeroxide P25) in methanol/acetonitrile (1:9) solvent under dry anoxic conditions led to hydrogenation and production of the corresponding succinimides. Aromatic and heteroaromatic aldehydes were reduced to primary alcohols in similar titania photocatalyzed reactions. A mechanism is proposed which involves two proton-coupled electron transfers to the substrates at the titania surface.

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Original languageEnglish
Pages (from-to)15324-15338
Number of pages15
JournalMolecules
Volume19
Issue number9
DOIs
StatePublished - 24 Sep 2014

    Research areas

  • Photocatalysis, Reduction, Titania, Maleimides, Aldehydes, Electron-deficient alkenes, Tertiary-amines, Radical-addition, Semiconductors, Photoaddition, Nanoparticles, Sensitizers, Alkylations, Complexes, Olefins

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