Electrochemical Ammoxidation of Unprotected Glycosides
Cyano-sugars are useful carbohydrate building blocks. Here, we report an electrocatalytic method to oxidize the primary alcohols of unprotected glycosides to the corresponding nitrile using 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) as a mediator and ammonium tetrafluoroborate as the ammonia source. Monosaccharides and disaccharides undergo successful reactions in an acetonitrile/pyridine solvent mixture at room temperature under constant current electrolysis.
Authors
- Mathew R. Johnson (ORCID: https://orcid.org/0000-0001-7456-6304)
- Martin D. Witte (ORCID: https://orcid.org/0000-0003-4660-2974)
- Adriaan J. Minnaard (ORCID: https://orcid.org/0000-0002-5966-1300)
- Sebastian B. Beil (ORCID: https://orcid.org/0000-0003-0373-3843)
- K. Jeya Prathap (ORCID: https://orcid.org/0000-0001-5602-6339)
- Md Asmaul Hoque (ORCID: https://orcid.org/0000-0003-3942-863X)
- Shannon S. Stahl (ORCID: https://orcid.org/0000-0002-9000-7665)
- Imke M. A. Bartels (ORCID: https://orcid.org/0009-0005-4105-2477)
Institutions
- University of Wisconsin–Madison (US)
- University of Groningen (NL)
- Max Planck Institute for Chemical Energy Conversion (DE)
Publication Details
- Journal
- ACS electrochemistry.
- Published
- 2025-05-15
- DOI
- https://doi.org/10.1021/acselectrochem.5c00111
- Citations
- 1
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Nederlandse Organisatie voor Wetenschappelijk Onderzoek
- National Institute of General Medical Sciences