One-pot aromatic amination based on carbon-nitrogen coupling reaction between aryl halides and azido compounds
One-pot aromatic amination based on carbon-nitrogen coupling reaction between aryl halides and azido compounds
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DOI：
10.1016/j.tet.2011.12.058
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发表时间：
2012-02-11
期刊：
影响因子：
2.1
通讯作者：
Sajiki, Hironao
中科院分区：
文献类型：
--
作者：
Maejima, Toshihide;Shimoda, Yutaka;Sajiki, Hironao
建立了一种有效的铜离子介导的芳基卤与叠氮化合物之间的C-N偶联反应，以生成相应的芳香伯胺。目前的胺化显然涉及叠氮基官能度还原为相应的伯氨基以及其与芳基卤以一锅方式的交叉偶联反应。该胺化反应可用于局部麻醉药普鲁卡因的合成。机理研究表明，2-氨基乙醇可以作为主要的氢供体，反应可以在不形成中间体芳基叠氮化物的情况下进行。(C)2011爱思唯尔有限公司版权所有，
An efficient copper-mediated C-N coupling reaction between various aryl halides and azido compounds to produce the corresponding aromatic primary amines was established. The present amination is apparently involved in both the reduction of an azido functionality to the corresponding primary amino group and its cross-coupling reaction with aryl halides in a one-pot manner. The present amination could be applied to the synthesis of procaine, a local anesthetic drug. A mechanistic study indicated that 2-aminoethanol could work as a major hydrogen donor and the reaction would proceed without the formation of the intermediary aryl azide. (C) 2011 Elsevier Ltd. All rights reserved,