Issue 47, 2018

Iron(iii) chloride-catalyzed activation of glycosyl chlorides

Abstract

Glycosyl chlorides have historically been activated using harsh conditions and/or toxic stoichiometric promoters. More recently, the Ye and the Jacobsen groups showed that glycosyl chlorides can be activated under organocatalytic conditions. However, those reactions are slow, require specialized catalysts and high temperatures, but still provide only moderate yields. Presented herein is a simple method for the activation of glycosyl chlorides using abundant and inexpensive ferric chloride in catalytic amounts. Our preliminary results indicate that both benzylated and benzoylated glycosyl chlorides can be activated with 20 mol% of FeCl3.

Graphical abstract: Iron(iii) chloride-catalyzed activation of glycosyl chlorides

Supplementary files

Article information

Article type
Communication
Submitted
27 Sep 2018
Accepted
06 Nov 2018
First published
06 Nov 2018

Org. Biomol. Chem., 2018,16, 9133-9137

Author version available

Iron(III) chloride-catalyzed activation of glycosyl chlorides

S. A. Geringer and A. V. Demchenko, Org. Biomol. Chem., 2018, 16, 9133 DOI: 10.1039/C8OB02413H

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