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异恶唑的电化学组装——一种四组分多米诺反应。

Electrochemical assembly of isoxazoles a four-component domino reaction.

作者信息

Zhao Yuanyuan, Li Xinyue, Homölle Simon L, Wang Bin, Ackermann Lutz

机构信息

Key Laboratory of Xin'an Medicine of the Ministry of Education, School of Pharmacy, Anhui University of Chinese Medicine Hefei 230038 P. R. China

Institut für Organische und Biomolekulare Chemie and Wöhler Research Institute for Sustainable Chemistry(WISCh), Georg-August-Universität Göttingen Tammannstraße 2 37077 Göttingen Germany

出版信息

Chem Sci. 2023 Dec 11;15(3):1117-1122. doi: 10.1039/d3sc05946d. eCollection 2024 Jan 17.

Abstract

Multicomponent domino reactions electrochemical annulations have emerged as a robust strategy for the rapid assembly of heterocyclics. Herein, an electrochemical annulation a [1 + 2 + 1 + 1] four-component domino reaction was accomplished in a user-friendly undivided cell setup to assemble valuable five-membered isoxazole motifs. Our approach is characterized by a high level functional group tolerance and operational simplicity, avoiding the tedious and time-consuming preparation of pre-functionalized substrates. Detailed mechanistic studies were conducted including isotopic labeling, kinetic studies, cyclic voltammetry (CV) analysis, and intermediate characterization, providing support for a radical pathway.

摘要

多组分多米诺反应和电化学环化反应已成为快速组装杂环化合物的一种可靠策略。在此,在一个用户友好的无隔膜电池装置中完成了一种电化学环化反应——[1 + 2 + 1 + 1]四组分多米诺反应,以组装有价值的五元异恶唑基序。我们的方法具有高度的官能团耐受性和操作简便性,避免了预官能化底物的繁琐且耗时的制备过程。进行了详细的机理研究,包括同位素标记、动力学研究、循环伏安法(CV)分析和中间体表征,为自由基途径提供了支持。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/180f/10793645/e2b600ed7974/d3sc05946d-f1.jpg

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