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通过芳基重氮盐的去重氮化反应实现的萘醌催化芳基胺的需氧加氢脱氨基反应。

-Naphthoquinone-Catalyzed Aerobic Hydrodeamination of Aryl Amines via De-diazotization of Aryl Diazonium Species.

作者信息

Si Tengda, Cho Hana, Kim Hun Young, Oh Kyungsoo

机构信息

Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul06974, Republic of Korea.

Department of Global Innovative Drugs, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul06974, Republic of Korea.

出版信息

Org Lett. 2022 Nov 25;24(46):8531-8535. doi: 10.1021/acs.orglett.2c03523. Epub 2022 Nov 10.

Abstract

The catalytic diazotization of aryl amines was developed using -naphthoquinone catalyst under aerobic conditions, where the 2-nitropropane served as a source of nitrosonium ion. The catalytic generation of diazonium species from aryl amines was further explored in the hydrode-diazotization to give the corresponding products. The mechanistic studies indicated the involvement of aryl radical species that readily underwent the radical cyclization to alkenes as well as the halogen abstraction reactions.

摘要

在有氧条件下,使用β-萘醌催化剂实现了芳基胺的催化重氮化反应,其中2-硝基丙烷作为亚硝基离子的来源。在加氢脱重氮化反应中进一步探索了由芳基胺催化生成重氮物种以得到相应产物。机理研究表明芳基自由基物种的参与,其易于发生自由基环化生成烯烃以及卤原子夺取反应。

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