Zhang, Bo, Guo, Tenglong, Li, Zhewei, Kuhn, Fritz E, Lei, Ming, Zhao, Zongbao K, Xiao, Jianliang 
ORCID: 0000-0003-2010-247X, Zhang, Jian, Xu, Dezhu, Zhang, Tao et al (show 1 more authors)
(2022)
Transition-metal-free synthesis of pyrimidines from lignin β-O-4 segments via a one-pot multi-component reaction.
NATURE COMMUNICATIONS, 13 (1).
3365-.
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Transition-metal-free synthesis of pyrimidines from lignin β-O-4 segments via a one-pot multi-component reaction.pdf - Published version Download (1MB) | Preview |
Abstract
Heteroatom-participated lignin depolymerization for heterocyclic aromatic compounds production is of great importance to expanding the product portfolio and meeting value-added biorefinery demand, but it is also particularly challenging. In this work, the synthesis of pyrimidines from lignin β-O-4 model compounds, the most abundant segment in lignin, mediated by NaOH through a one-pot multi-component cascade reaction is reported. Mechanism study suggests that the transformation starts by NaOH-induced deprotonation of Cα-H bond in β-O-4 model compounds, and involves highly coupled sequential cleavage of C-O bonds, alcohol dehydrogenation, aldol condensation, and dehydrogenative aromatization. This strategy features transition-metal free catalysis, a sustainable universal approach, no need of external oxidant/reductant, and an efficient one-pot process, thus providing an unprecedented opportunity for N-containing aromatic heterocyclic compounds synthesis from biorenewable feedstock. With this protocol, an important marine alkaloid meridianin derivative can be synthesized, emphasizing the application feasibility in pharmaceutical synthesis.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | Sodium Hydroxide, Transition Elements, Ethanol, Pyrimidines, Lignin, Oxidation-Reduction, Catalysis |
| Divisions: | Faculty of Science and Engineering > School of Physical Sciences |
| Depositing User: | Symplectic Admin |
| Date Deposited: | 22 Jul 2022 14:53 |
| Last Modified: | 14 Oct 2023 21:35 |
| DOI: | 10.1038/s41467-022-30815-5 |
| Open Access URL: | https://www.nature.com/articles/s41467-022-30815-5 |
| Related URLs: | |
| URI: | https://livrepository.liverpool.ac.uk/id/eprint/3159196 |
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