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三氟甲磺酸铟催化的两个亚胺单元的重排/环加成反应以及吖啶鎓光催化剂的后续模块化组装。

In(OTf)-catalyzed reorganization/cycloaddition of two imine units and subsequent modular assembly of acridinium photocatalysts.

作者信息

Nan Jiang, Huang Guanjie, Liu Shilei, Wang Jing, Ma Yangmin, Luan Xinjun

机构信息

The Youth Innovation Team of Shaanxi Universities, Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology Xi'an 710021 China

Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University Xi'an 710021 China.

出版信息

Chem Sci. 2023 Apr 17;14(19):5160-5166. doi: 10.1039/d3sc00163f. eCollection 2023 May 17.

Abstract

Herein, we disclose a novel reorganization/cycloaddition between two imine units catalyzed by In(OTf) Lewis acid that differs from the well-known [4 + 2] cycloaddition version the Povarov reaction. By means of this unprecedented imine chemistry, a collection of synthetically useful dihydroacridines has been synthesized. Notably, the obtained products give rise to a series of structurally novel and fine-tuneable acridinium photocatalysts, offering a heuristic paradigm for synthesis and efficiently facilitating several encouraging dihydrogen coupling reactions.

摘要

在此,我们揭示了一种由三氟甲磺酸铟(In(OTf))路易斯酸催化的、两个亚胺单元之间的新型重排/环加成反应,该反应不同于著名的[4 + 2]环加成反应——波瓦罗夫反应。通过这种前所未有的亚胺化学,合成了一系列具有合成价值的二氢吖啶。值得注意的是,所得到的产物产生了一系列结构新颖且可微调的吖啶鎓光催化剂,为合成提供了一种启发式范例,并有效地促进了几个令人鼓舞的二氢偶联反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dee6/10189902/7e51d4e1941b/d3sc00163f-s1.jpg

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