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Metallaphotocatalytic synthesis of anilines through tandem C–N transposition and C–H alkylation of alkylamines
Nature Synthesis Pub Date : 2023-07-27 , DOI: 10.1038/s44160-023-00370-y
Zhong-Wei Zhang , Zhe Feng , Jun-An Ma , Chi Wai Cheung

Alkylamines have a range of applications including as reagents in organic synthesis and as bioactive compounds in medicinal chemistry. Methods for the synthesis of alkylamines, however, typically suffer from low availability or inaccessibility of key reaction components and uncontrollable selectivity. While photocatalytic two-component reactions have become versatile strategies for the synthesis of alkylamines, multicomponent variants remain underdeveloped. Here we describe a metallaphotoredox-promoted three-component amination reaction using tertiary alkylamines, nitroarenes and carboxylic acids to give N-alkyl aniline products. The utility of this three-component approach is highlighted through the availability and broad scope of the reaction substrates and the application to the expedited synthesis of drug molecules and intermediates. Mechanistic investigations reveal this chemo- and regioselective transformation probably proceeds through a formal amine group transposition and C–H alkylation of a tertiary alkylamine substrate.



中文翻译:

通过串联 C-N 转位和烷基胺的 C-H 烷基化金属光催化合成苯胺

烷基胺具有广泛的应用,包括作为有机合成中的试剂和作为药物化学中的生物活性化合物。然而,烷基胺的合成方法通常存在关键反应组分的可用性低或难以获得以及选择性不可控的问题。虽然光催化双组分反应已成为合成烷基胺的通用策略,但多组分反应仍未得到开发。在这里,我们描述了金属光氧化还原促进的三组分胺化反应,使用叔烷基胺、硝基芳烃和羧酸来生成N-烷基苯胺产品。这种三组分方法的实用性通过反应底物的可用性和广泛范围以及在药物分子和中间体的快速合成中的应用而得到强调。机理研究表明,这种化学和区域选择性转化可能是通过叔烷基胺底物的形式胺基转座和 C-H 烷基化来进行的。

更新日期:2023-07-27
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