二乙基三胺五乙酸催化二氧化碳与胺的光催化 N-甲酰化反应

C Pub Date : 2024-07-11 DOI:10.3390/c10030062
Xuexin Yuan, Qiqi Zhou, Yu Chen, Haijian Yang, Q. Jiang, Juncheng Hu, Cunyue Guo
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摘要

在本研究中,以价格低廉、市场上可买到的二乙基三胺五乙酸(DTPA)为引发剂,在以黄酮为光敏剂、PhSiH3为还原剂的条件下,通过构建C-N键催化CO2与胺的N-甲酰化反应。经过对各种因素的系统研究,获得了光催化反应的最佳条件:2.5 毫摩尔胺、2.5 毫摩尔 PhSiH3、10 摩尔% 的 DTPA、20 摩尔% 的黄酮、1 毫升二甲基亚砜(DMSO)、常压和 35 瓦紫外灯照射 48 小时。在最佳条件下,该催化剂系统对胺(伯胺和仲胺)和 CO2 的 N-甲酰化具有很高的性能,二烷基胺的 N-甲酰化产物的收率高于 70%。进一步的研究表明,该催化系统具有广泛的底物应用范围。对于各种脂环族仲胺、杂环族仲胺、脂肪族伯胺和芳香族伯胺,都能高效地获得相应的 N-甲酰化产物。此外,催化剂还可以通过简单的沉淀和过滤进行循环利用。经过五次循环后,DTPA 的催化和结构特性没有发生明显变化。最后,还提出了一种可能的反应机理。
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Photocatalytic N-Formylation of CO2 with Amines Catalyzed by Diethyltriamine Pentaacetic Acid
In the present work, inexpensive and commercially available diethyltriamine pentaacetic acid (DTPA) was used as an initiator to catalyze the N-formylation reaction of CO2 with amines via the construction of C-N bonds in the presence of xanthone as the photosensitizer and PhSiH3 as the reducing agent. After a systematic study of various factors, the optimal conditions for the photocatalytic reaction were obtained: 2.5 mmol of amine, 2.5 mmol of PhSiH3, 10 mol% of DTPA, 20 mol% of xanthone, 1 mL of dimethylsulfoxide (DMSO), atmospheric pressure, and 35 W UV lamp irradiation for 48 h. Under the optimal conditions, the catalyst system afforded high performance for the N-formylation of amines (primary and secondary amines) and CO2, and the yields of the N-formylated products of dialkylamines were above 70%. Further studies exhibit that the catalytic system has a wide scope of substrate applications. For various alicyclic secondary amines, heterocyclic secondary amines, aliphatic primary amines, and aromatic primary amines, the corresponding N-formylation products can be obtained efficiently. In addition, the catalyst can be recycled by simple precipitation and filtration. After five cycles of recycling, there was no significant change in the catalytic and structural properties of DTPA. Finally, a possible reaction mechanism is proposed.
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