Iron(III) chloride-catalyzed activation of glycosyl chlorides
Iron(III) chloride-catalyzed activation of glycosyl chlorides
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DOI：
10.1039/c8ob02413h
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发表时间：
2018-12-21
影响因子：
3.2
通讯作者：
Demchenko, Alexei V.
中科院分区：
文献类型：
--
作者：
Geringer, Scott A.;Demchenko, Alexei V.
在历史上，使用苛刻的条件和/或有毒的化学计量促进剂来活化糖酰氯。最近，Ye和Jacobsen小组表明，糖基氯化物可以在有机催化条件下活化。然而，这些反应是缓慢的，需要专门的催化剂和高温，但仍然只能提供中等的产率。本文提出了一种使用催化量的丰富且廉价的氯化铁活化糖基氯化物的简单方法。我们的初步研究结果表明，苄基化和苯甲酰化的糖基氯化物可以被激活与20摩尔%的氯化铁。
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.