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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 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.

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Metadaten
Document Type:Article
Author:T. Schwob, Peter Kunnas, Niels de JongeORCiD, Christian PappORCiD, H.-P. Steinrück, Rhett KempeORCiD
URN:urn:nbn:de:bsz:291:415-4537
URL:https://advances.sciencemag.org/content/advances/5/11/eaav3680.full.pdf
DOI:https://doi.org/10.1126/sciadv.aav3680
ISSN:2375-2548
Parent Title (English):Science Advances
Volume:5
Issue:11
First Page:eaav3680
Language:English
Year of first Publication:2019
Release Date:2022/11/18
Impact:13.116 (2019)
Funding Information:Deutsche Forschungsgemeinschaft, KE 756/21-2
Scientific Units:Innovative Electron Microscopy
Open Access:Open Access
Signature:INM 2019/164
Licence (German):License LogoCreative Commons - CC BY-NC - Namensnennung - Nicht kommerziell 4.0 International