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General and selective deoxygenation by hydrogen using a reusable earth-abundant metal catalyst
Chemoselective deoxygenation by hydrogen is particularly challenging but crucial for an efficient late-stage modification of functionality-laden fine chemicals, natural products, or pharmaceuticals and the economic upgrading of biomass-derived molecules into fuels and chemicals. We report here on a...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Association for the Advancement of Science
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6858257/ https://www.ncbi.nlm.nih.gov/pubmed/31763445 http://dx.doi.org/10.1126/sciadv.aav3680 |
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author | Schwob, T. Kunnas, P. de Jonge, N. Papp, C. Steinrück, H.-P. Kempe, R. |
author_facet | Schwob, T. Kunnas, P. de Jonge, N. Papp, C. Steinrück, H.-P. Kempe, R. |
author_sort | Schwob, T. |
collection | PubMed |
description | Chemoselective deoxygenation by hydrogen is particularly challenging but crucial for an efficient late-stage modification of functionality-laden fine chemicals, natural products, or pharmaceuticals and the economic upgrading of biomass-derived molecules into fuels and chemicals. We report here on a reusable earth-abundant metal catalyst that permits highly chemoselective deoxygenation using inexpensive hydrogen gas. Primary, secondary, and tertiary alcohols as well as alkyl and aryl ketones and aldehydes can be selectively deoxygenated, even when part of complex natural products, pharmaceuticals, or biomass-derived platform molecules. The catalyst tolerates many functional groups including hydrogenation-sensitive examples. It is efficient, easy to handle, and conveniently synthesized from a specific bimetallic coordination compound and commercially available charcoal. Selective, sustainable, and cost-efficient deoxygenation under industrially viable conditions seems feasible. |
format | Online Article Text |
id | pubmed-6858257 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Association for the Advancement of Science |
record_format | MEDLINE/PubMed |
spelling | pubmed-68582572019-11-22 General and selective deoxygenation by hydrogen using a reusable earth-abundant metal catalyst Schwob, T. Kunnas, P. de Jonge, N. Papp, C. Steinrück, H.-P. Kempe, R. Sci Adv Research Articles Chemoselective deoxygenation by hydrogen is particularly challenging but crucial for an efficient late-stage modification of functionality-laden fine chemicals, natural products, or pharmaceuticals and the economic upgrading of biomass-derived molecules into fuels and chemicals. We report here on a reusable earth-abundant metal catalyst that permits highly chemoselective deoxygenation using inexpensive hydrogen gas. Primary, secondary, and tertiary alcohols as well as alkyl and aryl ketones and aldehydes can be selectively deoxygenated, even when part of complex natural products, pharmaceuticals, or biomass-derived platform molecules. The catalyst tolerates many functional groups including hydrogenation-sensitive examples. It is efficient, easy to handle, and conveniently synthesized from a specific bimetallic coordination compound and commercially available charcoal. Selective, sustainable, and cost-efficient deoxygenation under industrially viable conditions seems feasible. American Association for the Advancement of Science 2019-11-15 /pmc/articles/PMC6858257/ /pubmed/31763445 http://dx.doi.org/10.1126/sciadv.aav3680 Text en Copyright © 2019 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution NonCommercial License 4.0 (CC BY-NC). http://creativecommons.org/licenses/by-nc/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution-NonCommercial license (http://creativecommons.org/licenses/by-nc/4.0/) , which permits use, distribution, and reproduction in any medium, so long as the resultant use is not for commercial advantage and provided the original work is properly cited. |
spellingShingle | Research Articles Schwob, T. Kunnas, P. de Jonge, N. Papp, C. Steinrück, H.-P. Kempe, R. General and selective deoxygenation by hydrogen using a reusable earth-abundant metal catalyst |
title | General and selective deoxygenation by hydrogen using a reusable earth-abundant metal catalyst |
title_full | General and selective deoxygenation by hydrogen using a reusable earth-abundant metal catalyst |
title_fullStr | General and selective deoxygenation by hydrogen using a reusable earth-abundant metal catalyst |
title_full_unstemmed | General and selective deoxygenation by hydrogen using a reusable earth-abundant metal catalyst |
title_short | General and selective deoxygenation by hydrogen using a reusable earth-abundant metal catalyst |
title_sort | general and selective deoxygenation by hydrogen using a reusable earth-abundant metal catalyst |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6858257/ https://www.ncbi.nlm.nih.gov/pubmed/31763445 http://dx.doi.org/10.1126/sciadv.aav3680 |
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