Site-Selective Electrochemical Oxidation of Glycosides

Quinuclidine-mediated electrochemical oxidation of glycopyranosides provides C3-ketosaccharides with high selectivity and good yields. The method is a versatile alternative to Pd-catalyzed or photochemical oxidation and is complementary to the 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)-mediated C6...

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Bibliographic Details
Published in:ACS catalysis 2023-02, Vol.13 (4), p.2335-2340
Main Authors: Kidonakis, Marios, Villotet, Augustin, Witte, Martin D., Beil, Sebastian B., Minnaard, Adriaan J.
Format: Article
Language:English
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Summary:Quinuclidine-mediated electrochemical oxidation of glycopyranosides provides C3-ketosaccharides with high selectivity and good yields. The method is a versatile alternative to Pd-catalyzed or photochemical oxidation and is complementary to the 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)-mediated C6-selective oxidation. Contrary to the electrochemical oxidation of methylene and methine groups, the reaction proceeds without oxygen.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.2c06318