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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2014
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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. |
format | Online Article Text |
id | pubmed-6270841 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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