Catalytic Selective Oxidative Coupling of Secondary N-Alkylanilines: An Approach to Azoxyarene
Catalytic Selective Oxidative Coupling of Secondary N-Alkylanilines: An Approach to Azoxyarene
复制标题
仲 N-烷基苯胺的催化选择性氧化偶联：氧化偶氮芳烃的一种方法
DOI：
10.1021/acs.orglett.9b01200
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发表时间：
2019-06-07
期刊：
影响因子：
5.2
通讯作者：
Chen, Zhilong
中科院分区：
文献类型：
--
作者：
Ke, Lei;Zhu, Guirong;Chen, Zhilong
氧化偶氮芳烃是有机分子中重要的骨架。伯苯胺的直接氧化偶联提供了一种简洁的方式来构建它们。然而，这些支架是否可以从仲N-烷基苯胺制备还没有很好地探索。本文报道了在温和条件下，钨催化剂催化仲N-烷基苯胺选择性氧化偶联制备氧化偶氮芳烃。此外，氧化偶氮可被视为烯烃和酰胺的生物电子等排体。相应的生物活性烯烃和酰胺的几种“氧化偶氮芳烃类似物”显示出相当有前途的抗癌活性。
Azoxyarenes are among important scaffolds in organic molecules. Direct oxidative coupling of primary anilines provides a concise fashion to construct them. However, whether these scaffolds can be prepared from secondary N-alkylanilines is not well explored. Here, we present a catalytic selective oxidative coupling of secondary N-alkylaniline to afford azoxyarene with tungsten catalyst under mild conditions. In addition, azoxy can be viewed as a bioisostere of alkene and amide. Several "azoxyarene analogues" of the corresponding bioactive alkenes and amides showed comparable promising anticancer activities.