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吡啶氮在钯催化亚胺水解中的作用:(E)-1-(3-溴噻吩-2-基)-N-(4-甲基吡啶-2-基)甲亚胺的案例研究。

Role of Pyridine Nitrogen in Palladium-Catalyzed Imine Hydrolysis: A Case Study of (E)-1-(3-bromothiophen-2-yl)-N-(4-methylpyridin-2-yl)methanimine.

机构信息

Department of Chemistry, Government College University, Faisalabad 38000, Pakistan.

Department of Chemistry, Government College Women University, Faisalabad 38000, Pakistan.

出版信息

Molecules. 2019 Jul 17;24(14):2609. doi: 10.3390/molecules24142609.

Abstract

In the present study, 4-methylpyridin-2-amine was reacted with 3-bromothiophene-2-carbaldehyde and the Schiff base (E)-1-(3-bromothiophen-2-yl)-N-(4-methylpyridin-2-yl)methanimine was obtained in a 79% yield. Coupling of the Schiff base with aryl/het-aryl boronic acids under Suzuki coupling reaction conditions, using Pd(PPh) as catalyst, yielded products with the hydrolysis of the imine linkages (--) in good to moderate yields. To gain mechanistic insight into the transition metal-catalyzed hydrolysis of the compounds, density functional theory (DFT) calculations were performed. The theoretical calculations strongly supported the experiment and provided an insight into the transition metal-catalyzed hydrolysis of imines.

摘要

在本研究中,将 4-甲基吡啶-2-胺与 3-溴噻吩-2-甲醛反应,以 79%的收率得到席夫碱(E)-1-(3-溴噻吩-2-基)-N-(4-甲基吡啶-2-基)甲亚胺。在 Suzuki 偶联反应条件下,席夫碱与芳基/杂芳基硼酸偶联,使用 Pd(PPh)作为催化剂,得到了水解亚胺键(--)的产物,收率良好至中等。为了深入了解过渡金属催化水解化合物的机理,进行了密度泛函理论(DFT)计算。理论计算有力地支持了实验,并深入了解了亚胺的过渡金属催化水解。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a9a/6680400/3c432b77b223/molecules-24-02609-sch001.jpg

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