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. 2018 Dec 5;16(47):9133-9137.
doi: 10.1039/c8ob02413h.

Iron(iii) chloride-catalyzed activation of glycosyl chlorides

Scott A Geringer  1 , Alexei V Demchenko
Affiliations

Iron(iii) chloride-catalyzed activation of glycosyl chlorides

Scott A Geringer et al. Org Biomol Chem. .

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.

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Conflict of interest statement

Conflicts of interest

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1
Proposed mechanism of the activation of glycosyl chlorides with ferric chloride.
See this image and copyright information in PMC

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