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


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.

SUBMITTER: Zhang B 

PROVIDER: S-EPMC9188570 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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

Zhang Bo B   Guo Tenglong T   Li Zhewei Z   Kühn Fritz E FE   Lei Ming M   Zhao Zongbao K ZK   Xiao Jianliang J   Zhang Jian J   Xu Dezhu D   Zhang Tao T   Li Changzhi C  

Nature communications 20220611 1


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-in  ...[more]

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