Volume 8 Issue 2
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Article Navigation >  Green Energy&Environment  > 2023  >  8(2): 438-443
Cailing Wu, Mengjie Lou, Mingming Sun, Huiyong Wang, Zhiyong Li, Jikuan Qiu, Jianji Wang, Zhimin Liu. Selectively reductive amination of levulinic acid with aryl amines to N-substituted aryl pyrroles. Green Energy&Environment, 2023, 8(2): 438-443. doi: 10.1016/j.gee.2021.04.010
Citation: Cailing Wu, Mengjie Lou, Mingming Sun, Huiyong Wang, Zhiyong Li, Jikuan Qiu, Jianji Wang, Zhimin Liu. Selectively reductive amination of levulinic acid with aryl amines to N-substituted aryl pyrroles. Green Energy&Environment, 2023, 8(2): 438-443. doi: 10.1016/j.gee.2021.04.010
shu

Selectively reductive amination of levulinic acid with aryl amines to N-substituted aryl pyrroles

doi: 10.1016/j.gee.2021.04.010

  • a. Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University, Xinxiang, Henan, 453000, China;

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

Funds:

(Grant No. QYZDY-SSW-SLH013-2) and Henan Normal University, China.

This work was supported by Chinese Academy of Sciences, China

  • Received date 30 December 2020, Accepted date 21 April 2021, RevRecd date 14 April 2021, Publish date 24 April 2021,
    Abstract
  • Synthesizing nitrogen (N)-containing molecules from biomass derivatives is a new strategy for production of this kind of chemicals. Herein, for the first time we present the synthesis of N-substituted aryl pyrroles via reductive amination/cyclization of levulinic acid (LA) with primary aromatic amines and hydrosilanes (e.g., PMHS) over CsF, and a series of N-substituted aryl pyrroles could be obtained in good to excellent yields at 120 °C. The mechanism investigation indicates that the reaction proceeds in two steps: the cyclization between amine and LA occurs first to form intermediate 5-methyl-N-alkyl-1,3-dihydro-2H-pyrrolones and their isomeride ( B ), and then the chemo-and region-selective reduction of intermediates take place to produce the final products. This approach for synthesis of N-substituted aryl pyrroles can be performed under mild and green conditions, which may have promising applications.

     

    • • The synthesis of pyrroles via the selective reductive amination/cyclization of levulinic acid (LA) for the first time. • A serie of pyrroles were obtained in good to excellent yields at 120 °C within 5 h. • A reaction mechanism is proposed.
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