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用于水相中通过二硝基芳烃与醛的还原偶联一锅法合成苯并咪唑的多功能非均相钴催化剂

Multifunctional Heterogeneous Cobalt Catalyst for the One-Pot Synthesis of Benzimidazoles by Reductive Coupling of Dinitroarenes with Aldehydes in Water.

作者信息

Del Río-Rodríguez José Luis, Gutiérrez-Tarriño Silvia, Chinchilla Lidia E, Holgado Juan Pedro, Villar-García Ignacio J, Pérez-Dieste Virginia, Calvino Jose J, Oña-Burgos Pascual

机构信息

Instituto de Tecnología Química, Universitat Politècnica de València-Consejo Superior de Investigaciones Científicas (UPV-CSIC), Avda. de los Naranjos s/n, 46022, Valencia, Spain.

Departamento de Ciencia de los Materiales e Ingeniería Metalúrgica y Química Inorgánica, Facultad de Ciencias, Universidad de Cádiz, Campus Río San Pedro S/N, Puerto Real, 11510, Cádiz, Spain.

出版信息

ChemSusChem. 2025 Apr 14;18(8):e202402141. doi: 10.1002/cssc.202402141. Epub 2024 Dec 19.

Abstract

The endeavor of sustainable chemistry has led to significant advancements in green methodologies aimed at minimizing environmental impact while maximizing efficiency. Herein, a straightforward synthesis of benzimidazoles by reductive coupling of o-dinitroarenes with aldehydes is reported for the first time in aqueous media while using a non-noble metal catalyst. This work demonstrates that the combination of nitrogen and phosphorous ligands in the synthesis of supported heteroatom-incorporated Co nanoparticles is crucial for obtaining the desired benzimidazoles. The process achieves >99 % conversion, >99 % chemoselectivity and stability for the reduction of dinitroarenes using water as the solvent and hydrogen as the reductant under mild reaction conditions. The robustness of the catalyst has been investigated using several advanced techniques such as HRTEM, HAADF-STEM, XEDS, EELS, and NAP-XPS. In fact, we have shown that the introduction of N and P dopants prevents metal leaching and the sintering of the cobalt nanoparticles. Finally, to explore the general catalytic performance, a wide range of substituted dinitroarenes and benzaldehydes were evaluated, yielding benzimidazoles with competitive and scalable results, including MBIB (94 % yield), which is a compound of pharmaceutical interest.

摘要

可持续化学的努力已在绿色方法学方面取得了重大进展,旨在将环境影响降至最低,同时将效率最大化。在此,首次报道了在水介质中使用非贵金属催化剂通过邻二硝基芳烃与醛的还原偶联直接合成苯并咪唑。这项工作表明,在负载型杂原子掺杂钴纳米颗粒的合成中,氮和磷配体的组合对于获得所需的苯并咪唑至关重要。该过程在温和的反应条件下,以水为溶剂、氢气为还原剂,实现了二硝基芳烃还原的转化率>99%、化学选择性>99%以及稳定性。使用几种先进技术,如高分辨透射电子显微镜(HRTEM)、高角度环形暗场扫描透射电子显微镜(HAADF-STEM)、能量过滤X射线能谱(XEDS)、电子能量损失谱(EELS)和纳米角分辨光电子能谱(NAP-XPS)对催化剂的稳定性进行了研究。事实上,我们已经表明,氮和磷掺杂剂的引入可防止金属浸出和钴纳米颗粒的烧结。最后,为了探索一般催化性能,对多种取代的二硝基芳烃和苯甲醛进行了评估,得到了具有竞争力且可扩展结果的苯并咪唑,包括具有药物活性的化合物MBIB(产率94%)。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1b1/11997933/d26dda7d640f/CSSC-18-e202402141-g004.jpg

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