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金催化原位生成的α-氧代金卡宾在水中的串联环异构化/官能团化反应

Gold-catalyzed tandem cycloisomerization/functionalization of in situ generated α-oxo gold carbenes in water.

作者信息

Shen Cang-Hai, Li Long, Zhang Wei, Liu Shuang, Shu Chao, Xie Yun-Er, Yu Yong-Fei, Ye Long-Wu

机构信息

State Key Laboratory for Physical Chemistry of Solid Surfaces, The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University , Xiamen 361005, Fujian, P. R. China.

出版信息

J Org Chem. 2014 Oct 3;79(19):9313-8. doi: 10.1021/jo501872h. Epub 2014 Sep 25.

Abstract

A gold-catalyzed tandem cycloisomerization/functionalization of in situ generated α-oxo gold carbenes in water has been developed, which provides ready access to highly functionalized indole derivatives from o-alkynyl anilines and ynamides. Importantly, gold serves dual catalytic roles to mediate both the cycloisomerization of o-alkynyl anilines and the intermolecular oxidation of ynamides at the same time, thus providing a new type of concurrent tandem catalysis. The use of readily available starting materials, a simple procedure, and mild reaction conditions are other notable features of this method.

摘要

已开发出一种在水中对原位生成的α-氧代金卡宾进行金催化的串联环异构化/官能团化反应,该反应可从邻炔基苯胺和烯酰胺便捷地制得高度官能团化的吲哚衍生物。重要的是,金起到双重催化作用,同时介导邻炔基苯胺的环异构化和烯酰胺的分子间氧化,从而提供了一种新型的并发串联催化。使用易得的起始原料、操作简单以及反应条件温和是该方法的其他显著特点。

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