Transition‐Metal‐Free Valorization of Biomass‐derived Levulinic Acid Derivatives: Synthesis of Curcumene and Xanthorrhizol

Levulinic acid (LA) is acknowledged one of the most promising biomass‐derived platform molecules and can be transformed into various value‐added chemicals. Here, we report a new reaction process for the valorization of LA derivatives under transition‐metal‐free condition. The protocol combined with...

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Bibliographic Details
Published in:ChemSusChem 2021-02, Vol.14 (3), p.884-891
Main Authors: Xu, Wen‐Yan, Zhuo, Kai‐Feng, Gong, Tian‐Jun, Fu, Yao
Format: Article
Language:English
Subjects:
Acylation
Biomass
biomass conversion
Chemical synthesis
Coupling (molecular)
Cross coupling
Derivatives
Levulinic acid
levulinic acid derivatives
rac-curcumene
rac-xanthorrhizol
tosylhydrazone
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Summary:Levulinic acid (LA) is acknowledged one of the most promising biomass‐derived platform molecules and can be transformed into various value‐added chemicals. Here, we report a new reaction process for the valorization of LA derivatives under transition‐metal‐free condition. The protocol combined with the conversion of the levulinate to tosylhydrazone and base promoted arylation, acylation, and etherification cross‐coupling. Moreover, our method was applied to synthesize three biologically active molecules, rac‐curcumene, rac‐xanthorrhizol and rac‐4,7‐dimethyl‐l‐tetralone. This reaction discloses a new avenue for the high‐value utilization of platform molecules. Levulinic acid three ways: Metal‐free reductive cross‐coupling arylation, acylation, and etherification reactions of biomass‐derived levulinic acid derivative are reported. Three biologically active molecules, rac‐curcumene, rac‐xanthorrhizol, and rac‐4,7‐dimethyl‐l‐tetralone are accomplished by this method. This reaction provides a new route for the high‐value utilization of biomass platform molecules.
ISSN:1864-5631
1864-564X
DOI:10.1002/cssc.202002167