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Facile Access to Multiaryl-1H-pyrrol-2(3H)-ones by Copper/TEMPO-Mediated Cascade Annulation of Diarylethanones with Primary Amines and Mechanistic Insight
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2016-10-20 , DOI: 10.1002/ejoc.201601178
Xing Wang 1 , Chen-Yang Zhang 1 , Hai-Yang Tu 1 , Ai-Dong Zhang 1
Affiliation  

A straightforward approach to an array of multiaryl-1H-pyrrol-2(3H)-ones featuring an α-diarylated all-carbon quaternary center was developed by using diarylethanones and primary amines as the raw materials. A complete mechanism involving a CuO/TEMPO-mediated multistep cascade process with an inherent delicate balance of substituent electronic effect is proposed. Moreover, this class of multiaryl β,γ-unsaturated γ-lactams demonstrates an intriguing aggregation-induced emission effect valuable for potential application in developing luminescent materials.

中文翻译:

通过铜/TEMPO 介导的二芳基乙酮与伯胺的级联环化轻松获得多芳基-1H-吡咯-2(3H)-酮和机理洞察

通过使用二芳基乙烷和伯胺作为原料,开发了一种直接方法来制备一系列具有 α-二芳基化全碳季中心的多芳基-1H-吡咯-2(3H)-酮。提出了一种完整的机制,涉及 CuO/TEMPO 介导的多步级联过程,具有取代基电子效应的固有微妙平衡。此外,这类多芳基 β,γ-不饱和 γ-内酰胺表现出一种有趣的聚集诱导发射效应,对于开发发光材料的潜在应用很有价值。
更新日期:2016-10-20
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