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

Bo Zhang, Tenglong Guo, Zhewei Li, Fritz E. Kühn, Ming Lei, Zongbao K. Zhao, Jianliang Xiao, Jian Zhang, Dezhu Xu, Tao Zhang and Changzhi Li ()
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Bo Zhang: Chinese Academy of Sciences
Tenglong Guo: Chinese Academy of Sciences
Zhewei Li: Beijing University of Chemical Technology
Fritz E. Kühn: Technical University of Munich
Ming Lei: Beijing University of Chemical Technology
Zongbao K. Zhao: Chinese Academy of Sciences
Jianliang Xiao: University of Liverpool
Jian Zhang: Chinese Academy of Sciences
Dezhu Xu: Chinese Academy of Sciences
Tao Zhang: Chinese Academy of Sciences
Changzhi Li: Chinese Academy of Sciences

Nature Communications, 2022, vol. 13, issue 1, 1-11

Abstract: 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.

Date: 2022
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DOI: 10.1038/s41467-022-30815-5

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