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Insights for the hydrogen-mediated deoxydehydration (DODH) with Cp*ReO3 and alkene extrusion of related Re(V)-diolates

To transform highly oxygenated molecules such as polyols from biomass into value-added chemicals, the deoxygenation via the deoxydehydration (DODH) is a promising approach. We report the catalytic DODH of substrates from renewable resources using Cp*ReO3 (1 mol%, TON up to 32) as a catalyst and hydr...

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Main Authors: Stöckl, Yannick (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author) , Schaub, Thomas (Author)
Format: Article (Journal)
Language:English
Published: March 5, 2025
In: ChemCatChem
Year: 2025, Volume: 17, Issue: 7, Pages: 1-8
ISSN:1867-3899
DOI:10.1002/cctc.202402010
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/cctc.202402010
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/cctc.202402010
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Author Notes:Yannick Stöckl, Frank Rominger, A. Stephen K. Hashmi, Thomas Schaub
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Summary:To transform highly oxygenated molecules such as polyols from biomass into value-added chemicals, the deoxygenation via the deoxydehydration (DODH) is a promising approach. We report the catalytic DODH of substrates from renewable resources using Cp*ReO3 (1 mol%, TON up to 32) as a catalyst and hydrogen as a reductant. Additionally, the synthesis of Re(V)-diolates is described for tartrates, glycerol and erythritol derivatives. These Re(V)-diolates were obtained in 35-53% yield and as mixtures of diastereomers. Their characterization was accomplished using 2D NMR, MS, IR and X-ray diffraction. A NOESY study revealed an intermolecular exchange of glycerol moieties for the diolate complex. Further, alkene extrusion experiments allowed us to establish a reactivity order for a variety of substituents. The olefin extrusion was the fastest for tartrate units and the slowest for glycerol and erythritol diolates.
Item Description:Version der Veröffentlichung online: 05. März 2025
Gesehen am 02.12.2025
Physical Description:Online Resource
ISSN:1867-3899
DOI:10.1002/cctc.202402010

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