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Hydrogenations without Hydrogen: Titania Photocatalyzed Reductions of Maleimides and Aldehydes

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 co...

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Detalles Bibliográficos
Autores principales: Manley, David W., Buzzetti, Luca, MacKessack-Leitch, Andrew, Walton, John C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270841/
https://www.ncbi.nlm.nih.gov/pubmed/25255248
http://dx.doi.org/10.3390/molecules190915324
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author Manley, David W.
Buzzetti, Luca
MacKessack-Leitch, Andrew
Walton, John C.
author_facet Manley, David W.
Buzzetti, Luca
MacKessack-Leitch, Andrew
Walton, John C.
author_sort Manley, David W.
collection PubMed
description 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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spelling pubmed-62708412018-12-27 Hydrogenations without Hydrogen: Titania Photocatalyzed Reductions of Maleimides and Aldehydes Manley, David W. Buzzetti, Luca MacKessack-Leitch, Andrew Walton, John C. Molecules Article 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. MDPI 2014-09-24 /pmc/articles/PMC6270841/ /pubmed/25255248 http://dx.doi.org/10.3390/molecules190915324 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Manley, David W.
Buzzetti, Luca
MacKessack-Leitch, Andrew
Walton, John C.
Hydrogenations without Hydrogen: Titania Photocatalyzed Reductions of Maleimides and Aldehydes
title Hydrogenations without Hydrogen: Titania Photocatalyzed Reductions of Maleimides and Aldehydes
title_full Hydrogenations without Hydrogen: Titania Photocatalyzed Reductions of Maleimides and Aldehydes
title_fullStr Hydrogenations without Hydrogen: Titania Photocatalyzed Reductions of Maleimides and Aldehydes
title_full_unstemmed Hydrogenations without Hydrogen: Titania Photocatalyzed Reductions of Maleimides and Aldehydes
title_short Hydrogenations without Hydrogen: Titania Photocatalyzed Reductions of Maleimides and Aldehydes
title_sort hydrogenations without hydrogen: titania photocatalyzed reductions of maleimides and aldehydes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270841/
https://www.ncbi.nlm.nih.gov/pubmed/25255248
http://dx.doi.org/10.3390/molecules190915324
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