Highly efficient transformation of lignin major segments into quinolines
•A sustainable method to synthesize quinolines from lignin major segments has been successfully developed.•Redox-neutral depolymerization of lignin major segments and construction of quinoline motifs were realized in a one-pot fashion.•A tandem selective cleavage of C-O bonds/dehydrogenation/aza-Mic...
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| Published in | Chemical engineering science Vol. 290; p. 119899 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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15.05.2024
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| Abstract | •A sustainable method to synthesize quinolines from lignin major segments has been successfully developed.•Redox-neutral depolymerization of lignin major segments and construction of quinoline motifs were realized in a one-pot fashion.•A tandem selective cleavage of C-O bonds/dehydrogenation/aza-Michael addition/cyclization/dehydration/oxidation sequence is proposed.
The development of a sustainable synthesis route for functional quinolines from lignin β-O-4 segments containing γ-OH group is of high importance to meet biorefinery demands, but remains challenge due to the low cleavage efficiency of this specific motif and the incompatible catalytic systems. In this work a highly efficient transformation of β-O-4 lignin major segments into functional quinolines catalyzed by vanadium-based complex and copper has been developed, obtaining a wide range of substituted quinolines with good yields, which is a two-fold increase of quinolines yields when compared with previous sustainable routes. The pathway of this one-pot cascade reaction is investigated and a potential mechanism is proposed, involving the selective aryl ether cleavage, dehydrogenation, aza-Michael addition, dehydration and oxidation process. This work features a highly efficient transformation of lignin β-O-4 segments into N-heterocyclics without additional an oxidant or reductant agent, providing a concise and sustainable route for functional quinolines synthesis. |
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| AbstractList | •A sustainable method to synthesize quinolines from lignin major segments has been successfully developed.•Redox-neutral depolymerization of lignin major segments and construction of quinoline motifs were realized in a one-pot fashion.•A tandem selective cleavage of C-O bonds/dehydrogenation/aza-Michael addition/cyclization/dehydration/oxidation sequence is proposed.
The development of a sustainable synthesis route for functional quinolines from lignin β-O-4 segments containing γ-OH group is of high importance to meet biorefinery demands, but remains challenge due to the low cleavage efficiency of this specific motif and the incompatible catalytic systems. In this work a highly efficient transformation of β-O-4 lignin major segments into functional quinolines catalyzed by vanadium-based complex and copper has been developed, obtaining a wide range of substituted quinolines with good yields, which is a two-fold increase of quinolines yields when compared with previous sustainable routes. The pathway of this one-pot cascade reaction is investigated and a potential mechanism is proposed, involving the selective aryl ether cleavage, dehydrogenation, aza-Michael addition, dehydration and oxidation process. This work features a highly efficient transformation of lignin β-O-4 segments into N-heterocyclics without additional an oxidant or reductant agent, providing a concise and sustainable route for functional quinolines synthesis. |
| ArticleNumber | 119899 |
| Author | Skagfjörd Reinhold, Julian Guo, Tenglong Luo, Wenhao Zhu, Wenqing Zhang, Bo Lu, Jinfei Xu, Dezhu |
| Author_xml | – sequence: 1 givenname: Wenqing surname: Zhu fullname: Zhu, Wenqing organization: CAS Key Laboratory of Science and Technology On Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China – sequence: 2 givenname: Julian surname: Skagfjörd Reinhold fullname: Skagfjörd Reinhold, Julian organization: CAS Key Laboratory of Science and Technology On Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China – sequence: 3 givenname: Jinfei surname: Lu fullname: Lu, Jinfei organization: CAS Key Laboratory of Science and Technology On Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China – sequence: 4 givenname: Dezhu surname: Xu fullname: Xu, Dezhu organization: CAS Key Laboratory of Science and Technology On Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China – sequence: 5 givenname: Tenglong surname: Guo fullname: Guo, Tenglong email: guotl1210@dicp.ac.cn organization: CAS Key Laboratory of Science and Technology On Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China – sequence: 6 givenname: Wenhao surname: Luo fullname: Luo, Wenhao email: w.luo@imu.edu.cn organization: School of Chemistry and Chemical Engineering, Inner Mongolia University, 235 West University Street 010021, China – sequence: 7 givenname: Bo orcidid: 0000-0002-9140-7863 surname: Zhang fullname: Zhang, Bo email: bo.zhang@dicp.ac.cn organization: CAS Key Laboratory of Science and Technology On Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China |
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| Keywords | Quinolines V-based catalyst Lignin β-O-4 segments |
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