Journal
NATURE COMMUNICATIONS
Volume 13, Issue 1, Pages -Publisher
NATURE PORTFOLIO
DOI: 10.1038/s41467-022-30815-5
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Funding
- National Key R&D Program of China [2019YFC1905300]
- National Natural Science Foundation of China [22078317, 22108272, 22073005, 21721004, 21690083]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB17020100]
- 2017 Royal Society International Collaboration Award [IC170044]
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This study reports a novel method for synthesizing heterocyclic aromatic compounds from lignin, which is of great importance for expanding the product portfolio derived from biomass. The method is transition-metal free and sustainable, making it applicable for pharmaceutical synthesis.
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 beta-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 C alpha-H bond in beta-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. Lignin depolymerization to make heterocyclic aromatic compounds is of great importance to expanding the product portfolio derived from biomass, but it is also particularly challenging. In this work, the authors report pyrimidine synthesis from lignin beta-O-4 model compounds via a one-pot multicomponent cascade reaction.
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