A Copper‐Catalyzed Synthesis of Pyrroles through Photochemically Generated Acylazirines

A Copper‐Catalyzed Synthesis of Pyrroles through Photochemically Generated Acylazirines
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DOI:
10.1002/ejoc.201901176
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发表时间:
2019-11
影响因子:
2.8
通讯作者:
J. Paternoga;T. Opatz
J. Paternoga;T. Opatz
中科院分区:
化学3区
文献类型:
--
作者:
J. Paternoga;T. Opatz

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描述了通过光化学价异构化原位产生的酰基氮丙啶的铜催化二聚来合成高度取代的2,4-二酰基吡咯。所显示的方法允许使用简单的前体和易于获得的铜(II)催化剂。由于反应最好在高温下进行,因此建立了一种在光和金属诱导的双重过程中调节反应混合物温度的方法。此外,还进行了反应机理研究,以便更深入地了解 2-酰基氮丙啶的化学性质。
A synthesis of highly substituted 2,4‐diacylpyrroles through a Cu‐catalyzed dimerization of acylazirines generated in situ by a photochemical valence isomerization is described. The shown methodology allows the use of simple precursors and a readily available copper(II)‐catalyst. Since the reaction is best performed at elevated temperatures, a method to adjust the temperature of the reaction mixture during this dual light and metal‐induced process was established. Additionally, mechanistic studies of the reaction were performed in order to provide a deeper understanding of the chemistry of 2‐acylazirines.