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锚定在半胱氨酸功能化聚多巴胺包覆磁铁矿颗粒上的铜催化剂:用于增强偶联反应的通用平台。

Copper Catalysts Anchored on Cysteine-Functionalized Polydopamine-Coated Magnetite Particles: A Versatile Platform for Enhanced Coupling Reactions.

作者信息

Jo Yu-Jeong, Park Seung-Woo, Shin Ueon Sang, Kim Seung-Hoi

机构信息

Department of Chemistry, Dankook University, Cheonan 31116, Republic of Korea.

Department of Nanobiomedical Science, BK21 FOUR NBM Global Research Center for Regenerative Medicine, Dankook University, Cheonan 31116, Republic of Korea.

出版信息

Molecules. 2024 Oct 30;29(21):5121. doi: 10.3390/molecules29215121.

Abstract

Cysteine plays a crucial role in the development of an efficient copper-catalyst system, where its thiol group serves as a strong anchoring site for metal coordination. By immobilizing copper onto cysteine-modified, polydopamine-coated magnetite particles, this advanced catalytic platform exhibits exceptional stability and catalytic activity. Chemical modification of the polydopamine (PDA) surface with cysteine enhances copper salt immobilization, leading to the formation of the FeO@PDA-Cys@Cu platform. This system was evaluated in palladium-free, copper-catalyzed Sonogashira coupling reactions, effectively catalyzing the coupling of terminal acetylenes with aryl halides. Additionally, the FeO@PDA-Cys@Cu platform was employed in click reactions, confirming the enhanced catalytic efficiency due to increased copper content. The reusability of the platform was further investigated, demonstrating improved performance, especially in recyclability tests in click reaction, making it a promising candidate for sustainable heterogeneous catalysis.

摘要

半胱氨酸在高效铜催化体系的发展中起着至关重要的作用,其硫醇基团作为金属配位的强锚定位点。通过将铜固定在半胱氨酸修饰的聚多巴胺包覆的磁铁矿颗粒上,这种先进的催化平台表现出卓越的稳定性和催化活性。用半胱氨酸对聚多巴胺(PDA)表面进行化学修饰可增强铜盐的固定,从而形成FeO@PDA-Cys@Cu平台。该体系在无钯铜催化的Sonogashira偶联反应中进行了评估,有效地催化了末端乙炔与芳基卤化物的偶联。此外,FeO@PDA-Cys@Cu平台被用于点击反应,证实了由于铜含量增加而提高的催化效率。进一步研究了该平台的可重复使用性,结果表明其性能有所改善,特别是在点击反应的循环利用测试中,使其成为可持续多相催化的一个有前途的候选者。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/af8c/11547350/3b018a79878e/molecules-29-05121-g001.jpg

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