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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 1: 53 - 60

DOI: https://doi.org/10.6023/cjoc201908017

Half-Sandwich Ruthenium(II) Complexes with Bidentate NN Ligands:Active Catalysts for the Synthesis of Quinolines and Pyrroles by Acceptorless Dehydrogenative Cyclization

  • Hu Bowen ,
  • Zhang Yuzhe ,
  • Yin Geping ,
  • Chen Dafa
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  • School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001

Received date: 2019-08-11

  Revised date: 2019-09-16

  Online published: 2019-09-25

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21672045, 21871068), the China Postdoctoral Science Foundation (No. 2016M591519), the Heilongjiang Provincial Postdoctoral Foundation (No. LBH-Z16069), and the National Natural Science Foundation of Heilongjiang Province (Nos. B2018005, LC2018005).

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Abstract

Four (h6-p-cymene)Ru(II) complexes with bidentate NN ligands, (h6-p-cymene)Ru(C5H4N-C5H3N-OH) (1), (h6-p-cymene)Ru(C5H4N-CH2-C5H4N) (2), (h6-p-cymene)Ru(C5H4N-CH2-C5H3N-OH) (3) and (h6-p-cymene)Ru(C5H4N-CH2-C5H3N-OCH3) (4) were prepared. These complexes were all characterized by1H NMR, 13C NMR and elemental analysis, and complex 2 was further determined by single crystal crystallography. Complexes 1~4 were treated as catalysts for cyclizations of amino alcohols with ketones, and complex 3 exhibited the highest activity. The cyclization reactions proceeded in toluene with 0.5 mol% catalyst loading, and a series of quinolines and pyrroles were synthesized.

Key words： half-sandwich; ruthenium; acceptorless dehydrogenative cyclization; bidentate ligand; 2-hydroxypyridine

Cite this article

Hu Bowen , Zhang Yuzhe , Yin Geping , Chen Dafa . Half-Sandwich Ruthenium(II) Complexes with Bidentate NN Ligands:Active Catalysts for the Synthesis of Quinolines and Pyrroles by Acceptorless Dehydrogenative Cyclization[J]. Chinese Journal of Organic Chemistry, 2020 , 40(1) : 53 -60 . DOI: 10.6023/cjoc201908017

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