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-aryl 吩噻嗪和吩恶嗪的简便合成 Brønsted 酸催化芳烃的 C-H 氨化反应。

Facile synthesis of -aryl phenothiazines and phenoxazines Brønsted acid catalyzed C-H amination of arenes.

机构信息

Shenzhen Grubbs Institute, Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China.

Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen 518055, China.

出版信息

Chem Commun (Camb). 2022 Feb 1;58(10):1613-1616. doi: 10.1039/d1cc06730c.

Abstract

-Aryl phenothiazines and phenoxazines are of significant importance in various disciplines throughout academia and industry. The conventional synthetic strategy for the construction of these structures centers on the transition-metal-catalyzed cross-coupling of aryl halides with phenothiazines or phenoxazines. Here we present an organocatalytic approach to access -naphthyl phenothiazine and phenoxazine scaffolds through a straightforward C-H amination of arenes as enabled by an azo group. This reaction features operational simplicity, adequate substrate generality and excellent functional group compatibility. Notably, the efficiency of the catalyst could be perfectly preserved after 5 catalytic cycles.

摘要

芳基吩噻嗪和吩恶嗪在学术界和工业界的各个领域都具有重要意义。这些结构的传统合成策略集中在芳基卤化物与吩噻嗪或吩恶嗪的过渡金属催化交叉偶联上。在这里,我们提出了一种通过芳基的简单 C-H 氨化来获得 -萘基吩噻嗪和吩恶嗪骨架的有机催化方法,这是通过偶氮基团实现的。该反应具有操作简单、底物通用性好和官能团兼容性好的特点。值得注意的是,催化剂的效率在 5 个催化循环后仍能完美保持。

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