Selectively reductive amination of levulinic acid with aryl amines to N-substituted aryl pyrroles
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 amin...
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| Format: | Article |
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KeAi Communications Co., Ltd.
2023-04-01
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| Series: | Green Energy & Environment |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2468025721000868 |
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| author | Cailing Wu Mengjie Lou Mingming Sun Huiyong Wang Zhiyong Li Jikuan Qiu Jianji Wang Zhimin Liu |
| author_facet | Cailing Wu Mengjie Lou Mingming Sun Huiyong Wang Zhiyong Li Jikuan Qiu Jianji Wang Zhimin Liu |
| author_sort | Cailing Wu |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-09T23:39:20Z |
| format | Article |
| id | doaj.art-55846586084040469b0055b1b9d91a77 |
| institution | Directory Open Access Journal |
| issn | 2468-0257 |
| language | English |
| last_indexed | 2024-04-09T23:39:20Z |
| publishDate | 2023-04-01 |
| publisher | KeAi Communications Co., Ltd. |
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| series | Green Energy & Environment |
| spelling | doaj.art-55846586084040469b0055b1b9d91a772023-03-19T04:38:11ZengKeAi Communications Co., Ltd.Green Energy & Environment2468-02572023-04-0182438443Selectively reductive amination of levulinic acid with aryl amines to N-substituted aryl pyrrolesCailing Wu0Mengjie Lou1Mingming Sun2Huiyong Wang3Zhiyong Li4Jikuan Qiu5Jianji Wang6Zhimin Liu7Collaborative 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, ChinaCollaborative 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, ChinaCollaborative 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, ChinaCollaborative 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, ChinaCollaborative 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, ChinaCollaborative 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, ChinaCollaborative 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; Corresponding authors.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; Corresponding authors.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.http://www.sciencedirect.com/science/article/pii/S2468025721000868BiomassLevulinic acidReductive aminationPyrrole |
| spellingShingle | 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 Biomass Levulinic acid Reductive amination Pyrrole |
| title | Selectively reductive amination of levulinic acid with aryl amines to N-substituted aryl pyrroles |
| title_full | Selectively reductive amination of levulinic acid with aryl amines to N-substituted aryl pyrroles |
| title_fullStr | Selectively reductive amination of levulinic acid with aryl amines to N-substituted aryl pyrroles |
| title_full_unstemmed | Selectively reductive amination of levulinic acid with aryl amines to N-substituted aryl pyrroles |
| title_short | Selectively reductive amination of levulinic acid with aryl amines to N-substituted aryl pyrroles |
| title_sort | selectively reductive amination of levulinic acid with aryl amines to n substituted aryl pyrroles |
| topic | Biomass Levulinic acid Reductive amination Pyrrole |
| url | http://www.sciencedirect.com/science/article/pii/S2468025721000868 |
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