Missing-linker defects in a covalent organic framework photocatalyst for highly efficient synthesis of tetrahydroquinoline,Green Chemistry

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Missing-linker defects in a covalent organic framework photocatalyst for highly efficient synthesis of tetrahydroquinoline
Green Chemistry ( IF 9.3 ) Pub Date : 2024-01-10 , DOI: 10.1039/d3gc04566h
Yuling Zhao ₁ , Kangna Zhang ₁ , Keping Zhu ₁ , Yaqin Zhao ₁ , Hanping Zhai ₁ , Jikuan Qiu ₁

Affiliation

Cyclization of N,N-dimethylanilines with maleimides to obtain tetrahydroquinoline heterocyclic compounds is an essential reaction in industry but it is usually catalyzed by noble-metal catalysts under harsh conditions. High-performance, metal-free, low-cost, stable porous photocatalysts can provide an efficient pathway for the green synthesis of tetrahydroquinolines. Herein, we present a unique imine-based covalent organic framework, COF-HNU30-10, with good stability and a high density of structural defects for the selective cyclization of N,N-dimethylanilines with maleimides. Experiments show that various tetrahydroquinolines can be quantitatively synthesized (yield > 99.9%) using COF-HNU30-10 as a catalyst under visible-light irradiation. Such a yield is significantly higher than that (yield of 49%) obtained using a non-defective COFHNU30-0 and even higher than that obtained with Pt and Ru-based heterogeneous catalysts. A mechanistic study reveals that the introduction of defects in the framework facilitates the charge transfer and separation states, thus resulting in an enhancement of photocatalytic activity. Moreover, COF-HNU30-10 achieved a benchmark balance between the photocatalytic performance, stability and cost-effectiveness for the quantitative synthesis of tetrahydroquinolines.

中文翻译：

用于高效合成四氢喹啉的共价有机骨架光催化剂中的缺失连接体缺陷

N , N-二甲基苯胺与马来酰亚胺环化生成四氢喹啉杂环化合物是工业上必不可少的反应，但通常需要贵金属催化剂在恶劣的条件下催化。高性能、无金属、低成本、稳定的多孔光催化剂可以为四氢喹啉的绿色合成提供有效途径。在此，我们提出了一种独特的亚胺基共价有机骨架COF-HNU30-10，具有良好的稳定性和高密度的结构缺陷，用于N , N-二甲基苯胺与马来酰亚胺的选择性环化。实验表明，在可见光照射下，以COF-HNU30-10为催化剂，可以定量合成多种四氢喹啉（收率>99.9%）。这样的产率明显高于使用无缺陷COFHNU30-0获得的产率（49%的产率），甚至高于使用Pt和Ru基多相催化剂获得的产率。机理研究表明，框架中引入缺陷有利于电荷转移和分离状态，从而增强光催化活性。此外，COF-HNU30-10在四氢喹啉定量合成中实现了光催化性能、稳定性和成本效益之间的基准平衡。

更新日期：2024-01-10

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