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二恶唑,金催化中一种新型温和的氮烯转移试剂:功能化恶唑的高效合成。

Dioxazoles, a new mild nitrene transfer reagent in gold catalysis: highly efficient synthesis of functionalized oxazoles.

作者信息

Chen Ming, Sun Ning, Chen Haoyi, Liu Yuanhong

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

出版信息

Chem Commun (Camb). 2016 May 7;52(37):6324-7. doi: 10.1039/c6cc02776h. Epub 2016 Apr 18.

Abstract

A gold-catalyzed regioselective [3+2] cycloaddition of ynamides with 1,4,2-dioxazoles was developed and offers a novel approach to obtain highly functionalized oxazoles under mild reaction conditions. 1,4,2-Dioxazole was found to act as an efficient N-acyl nitrene equivalent to trigger a facile generation of α-imino gold-carbene intermediate through the elimination of a ketone.

摘要

开发了一种金催化的烯酰胺与1,4,2-二恶唑的区域选择性[3+2]环加成反应,为在温和反应条件下获得高度官能化的恶唑提供了一种新方法。发现1,4,2-二恶唑可作为一种有效的N-酰基氮烯等价物,通过消除酮来引发α-亚氨基金-卡宾中间体的轻松生成。

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