Site-Selective Electrochemical Oxidation of Glycosides

Marios Kidonakis; Augustin Villotet; Martin D Witte; Sebastian B Beil; Adriaan J Minnaard

doi:10.1021/acscatal.2c06318

Site-Selective Electrochemical Oxidation of Glycosides

ACS Catal. 2023 Jan 31;13(4):2335-2340. doi: 10.1021/acscatal.2c06318. eCollection 2023 Feb 17.

Authors

Marios Kidonakis¹, Augustin Villotet¹, Martin D Witte¹, Sebastian B Beil¹, Adriaan J Minnaard¹

Affiliation

¹ Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG Groningen, The Netherlands.

Abstract

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.