Ruthenium-catalyzed divergent deaminative and denitrative C–N cleavages: facile access to quinoxalines,Organic Chemistry Frontiers

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Ruthenium-catalyzed divergent deaminative and denitrative C–N cleavages: facile access to quinoxalines
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2022-11-16 , DOI: 10.1039/d2qo01572b
Shanshan Liu ₁ , Jiahui Liang ₁ , Pingjun Zhang ₁ , Zhenzhen Li ₁ , Lin-Yu Jiao ₂ , Wei Jia ₁ , Yangmin Ma ₁ , Michal Szostak _{1,

3}

Affiliation

Divergent deaminative and denitrative C–N cleavages and cascade transformations using amines and nitroalkanes have been developed under a highly effective and environmentally-friendly catalytic system (RuCl₃/TFE). This protocol provides a versatile toolbox for the construction of quinoxalines under redox-neutral and mild conditions. Specifically, Ru-catalyzed acceptorless dehydrogenation and hydrogen borrowing strategies have been successfully implemented in the activation of amines, which is distinct from the dehydrogenation of frequently used alcohol as a hydrogen donor, enabling the deaminative coupling of amines with 2-arylanilines and 2-nitroarylpyrroles in the absence of additives. Crucially, unprecedented Ru-catalyzed denitrative C–NO₂ cleavages have been realized, wherein nitroalkanes were explored as unconventional electrophilic C synthons to accomplish [5 + 1] annulation. This identified process features exceedingly simple, environmentally-friendly conditions, ease of operation, a broad substrate scope, and the capacity to synthesise antileishmanial agents and bipolar host materials for OLEDs.

中文翻译：

钌催化的不同脱氨和脱硝 C-N 裂解：容易获得喹喔啉

在高效环保的催化系统 (RuCl ₃ /TFE) 下，开发了使用胺和硝基烷烃的不同脱氨和反硝化 C-N 裂解和级联转化。该协议为在氧化还原中性和温和条件下构建喹喔啉提供了一个多功能工具箱。具体而言，Ru 催化的无受体脱氢和借氢策略已成功应用于胺的活化，这与常用的醇作为氢供体的脱氢不同，能够使胺与 2-芳基苯胺和 2-硝基芳基吡咯脱氨偶联在没有添加剂的情况下。至关重要的是，前所未有的 Ru 催化反硝化 C–NO ₂裂解已经实现，其中硝基烷烃被探索为非常规的亲电子 C 合成子以完成 [5 + 1] 环化。这一确定的工艺具有极其简单、环境友好的条件、易于操作、广泛的底物范围以及为 OLED 合成抗利什曼氏菌剂和双极主体材料的能力。

更新日期：2022-11-16

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