Issue 9, 2021

Palladium(ii)-assisted activation of thioglycosides

Abstract

Described herein is the first example of glycosidation of thioglycosides in the presence of palladium(II) bromide. While the activation with PdBr2 alone was proven feasible, higher yields and cleaner reactions were achieved when these glycosylations were performed in the presence of propargyl bromide as an additive. Preliminary mechanistic studies suggest that propargyl bromide assists the reaction by creating an ionizing complex, which accelerates the leaving group departure. A variety of thioglycoside donors in reactions with different glycosyl acceptors were investigated to determine the initial scope of this new reaction. Selective and chemoselective activation of thioglycosides over other leaving groups has also been explored.

Graphical abstract: Palladium(ii)-assisted activation of thioglycosides

Supplementary files

Article information

Article type
Paper
Submitted
01 Jan 2021
Accepted
10 Feb 2021
First published
11 Feb 2021

Org. Biomol. Chem., 2021,19, 2044-2054

Author version available

Palladium(II)-assisted activation of thioglycosides

S. Escopy, Y. Singh and A. V. Demchenko, Org. Biomol. Chem., 2021, 19, 2044 DOI: 10.1039/D1OB00004G

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