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用于喹啉和四氢喹啉一锅合成的半夹心钌配合物:在偶联环化和氢化过程中具有多样的催化活性。

Half-Sandwich Ruthenium Complexes for One-Pot Synthesis of Quinolines and Tetrahydroquinolines: Diverse Catalytic Activity in the Coupled Cyclization and Hydrogenation Process.

机构信息

School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China.

State Key Laboratory of Transducer Technology, Shanghai Institute of Microsystem and Information Technology, Chinese Academy of Sciences, Shanghai 200050, China.

出版信息

Inorg Chem. 2020 Jun 1;59(11):7841-7851. doi: 10.1021/acs.inorgchem.0c00955. Epub 2020 May 12.

DOI:10.1021/acs.inorgchem.0c00955
PMID:32396339
Abstract

Four types of half-sandwich ruthenium complexes with an N,O-coordinate mode based on hydroxyindanone-imine ligands have been prepared in good yields. These stable ruthenium complexes exhibited high activity in the catalytic synthesis of quinolines from the reactions of amino alcohols with different types of ketones or secondary alcohols under very mild conditions. Moreover, the methodology for the direct one-pot synthesis of tetrahydroquinoline derivatives from amino alcohols and ketones has been also developed on the basis of the continuous catalytic activity of this ruthenium catalyst in the selective hydrogenation of the obtained quinoline derivatives with a low catalyst loading. The corresponding products, quinolines and tetrahydroquinoline derivatives, were afforded in good to excellent yields. The efficient and diverse catalytic activity of these ruthenium complexes suggested their potential large-scale application. All of the ruthenium complexes were characterized by various spectroscopies to confirm their structures.

摘要

已成功制备了四种基于羟基茚满酮-亚胺配体的 N,O-配位模式的半三明治型钌配合物,产率较高。这些稳定的钌配合物在温和条件下,通过不同类型的酮或仲醇与氨基醇的反应,表现出催化合成喹啉的高活性。此外,基于该钌催化剂在选择性加氢得到的喹啉衍生物中具有连续催化活性,还开发了一种直接一锅法从氨基醇和酮合成四氢喹啉衍生物的方法,催化剂的用量较低。相应的产物喹啉和四氢喹啉衍生物以良好至优秀的收率得到。这些钌配合物具有高效和多样的催化活性,表明它们具有潜在的大规模应用前景。所有的钌配合物都通过各种光谱学方法进行了表征,以确认其结构。

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引用本文的文献

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Synthesis of Tetrahydroquinolines via Borrowing Hydrogen Methodology Using a Manganese PN Pincer Catalyst.通过锰 PN 钳形催化剂的借氢方法合成四氢喹啉。
Org Lett. 2020 Oct 16;22(20):7964-7970. doi: 10.1021/acs.orglett.0c02905. Epub 2020 Sep 24.