Transition-metal-free synthesis of pyrimidines from lignin β-O-4 segments via a one-pot multi-component reaction



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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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