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N-methylation of quinolines with CO2 and H2 catalyzed by Ru-triphos complexes

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Abstract

N-methyl-tetrahydroquinolines (MTHQs) are a kind of very useful chemicals, which can be obtained from N-methylation of amines. However, the methylation of quinolines which is a kind of highly unsaturated nitrogen-containing heterocyclic aromatic compounds has not been reported. In this work, we report the first work for the synthesis of MTHQs by methylation of quinolines using CO2 and H2. It was found that Ru(acac)3-triphos [triphos: 1,1,1-tris(diphenylphosphinomethyl)ethanl] complex was very active and selective for the N-methylation reaction of quinolines, and the yield of the desired product could reach 99%.

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Acknowledgments

This work was supported by National Natural Science Foundation of China (21603235, 21373234, 21533011), Chinese Academy of Sciences (QYZDY-SSW-SLH013) and the Recruitment Program of Global Youth Experts of China.

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Authors and Affiliations

  1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid and Interface and Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China

    Zhenhong He, Huizhen Liu, Qingli Qian, Lu Lu, Weiwei Guo, Lujun Zhang & Buxing Han

  2. University of Chinese Academy of Sciences, Beijing, 100049, China

    Huizhen Liu & Buxing Han

  3. College of Chemistry and Chemical Engineering, Shaanxi University of Science & Technology, Xi’an, 710021, China

    Zhenhong He

Authors
  1. Zhenhong He
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  2. Huizhen Liu
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  3. Qingli Qian
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  4. Lu Lu
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  5. Weiwei Guo
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  6. Lujun Zhang
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  7. Buxing Han
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Correspondence to Huizhen Liu or Buxing Han.

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He, Z., Liu, H., Qian, Q. et al. N-methylation of quinolines with CO2 and H2 catalyzed by Ru-triphos complexes. Sci. China Chem. 60, 927–933 (2017). https://doi.org/10.1007/s11426-017-9024-8

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  • DOI: https://doi.org/10.1007/s11426-017-9024-8

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