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Iron(III) chloride-catalyzed activation of glycosyl chlorides

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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

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Publication details

The article was received on 27 Sep 2018, accepted on 06 Nov 2018 and first published on 06 Nov 2018


Article type: Communication
DOI: 10.1039/C8OB02413H
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Iron(III) chloride-catalyzed activation of glycosyl chlorides

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

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