Investigation of the Role of Electrogenerated N-Heterocyclic Carbene in the Staudinger Synthesis in Ionic Liquid
Investigation of the Role of Electrogenerated N-Heterocyclic Carbene in the Staudinger Synthesis in Ionic Liquid
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DOI：
10.4236/ijoc.2011.14028
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发表时间：
2011-12
影响因子：
2.1
通讯作者：
M. Feroci
中科院分区：
文献类型：
--
作者：
M. Feroci
在离子液体中，由Bmim-BF 4阴极还原得到的电生成的N-杂环卡宾（NHC）在由酰氯和失活的亚胺进行的Staudinger合成中表现为有机催化剂和碱，以生成？-内酰胺。许多参数（温度，电量，取代基，外部碱的存在下）的效果进行了评估和Staudinger合成在一个非常极性的介质，如离子液体报告的一个试探性的机制。孤立的产量？-从非亲电子亚胺开始，内酰胺是好的，并且主要以良好的非对映异构体比例获得反式内酰胺。
Electrogenerated N-heterocyclic carbene (NHC), obtained by cathodic reduction of Bmim-BF4, behaves as organocatalyst and base in the Staudinger synthesis from an acyl chloride and a deactivated imine in ionic liquid to yield ?-lactams. The effect of many parameters (temperature, amount of electricity, substituents, presence of an external base) has been evaluated and a tentative mechanism for the Staudinger synthesis in a very polar medium like the ionic liquid reported. The yields of isolated ?-lactams are good, starting from non-electrophilic imines, and predominantly trans lactams are obtained with a good diastereomeric ratio.