使用稳定的N-氯代亚胺和叔丁醇锂对醚进行区域选择性α-胺化反应。
Regioselective α-Amination of Ethers Using Stable N-Chloroimides and Lithium tert-Butoxide.
作者信息
Gasonoo Makafui, Thom Zachary W, Laulhé Sébastien
机构信息
Department of Chemistry and Chemical Biology , Indiana University-Purdue University Indianapolis (IUPUI) , Indianapolis , Indiana 46202 , United States.
出版信息
J Org Chem. 2019 Jul 5;84(13):8710-8716. doi: 10.1021/acs.joc.9b00824. Epub 2019 Jun 19.
Abstract
Herein we describe a metal-free regioselective α-amination of ethers mediated by N-chloroimides in ethereal solvents in the presence of lithium tert-butoxide. This reactivity of N-chloroimides leads to the synthesis of hemiaminal ethers in good to excellent yields at room temperature. This C-H functionalization is achieved without the use of a light, heat source, or external radical initiators. Initial mechanistic work indicates that the reaction proceeds through a radical pathway.
摘要
在此，我们描述了在叔丁醇锂存在下，N-氯代酰亚胺在醚类溶剂中介导的醚的无金属区域选择性α-胺化反应。N-氯代酰亚胺的这种反应性能够在室温下以良好至优异的产率合成半缩醛胺醚。这种C-H官能化反应无需使用光、热源或外部自由基引发剂即可实现。初步的机理研究表明，该反应通过自由基途径进行。
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