Selective lignin arylation for biomass fractionation and benign bisphenols

Ning Li, Kexin Yan, Thanya Rukkijakan, Jiefeng Liang, Yuting Liu, Zhipeng Wang, Heran Nie, Suthawan Muangmeesri, Gonzalo Castiella-Ona, Xuejun Pan, Qunfang Zhou, Guibin Jiang, Guangyuan Zhou, John Ralph, Joseph S. M. Samec () and Feng Wang ()
Additional contact information
Ning Li: Chinese Academy of Sciences
Kexin Yan: Chinese Academy of Sciences
Thanya Rukkijakan: Stockholm University
Jiefeng Liang: Chinese Academy of Sciences
Yuting Liu: Chinese Academy of Sciences
Zhipeng Wang: Chinese Academy of Sciences
Heran Nie: Chinese Academy of Sciences
Suthawan Muangmeesri: Stockholm University
Gonzalo Castiella-Ona: Stockholm University
Xuejun Pan: University of Wisconsin-Madison
Qunfang Zhou: Chinese Academy of Sciences
Guibin Jiang: Chinese Academy of Sciences
Guangyuan Zhou: Chinese Academy of Sciences
John Ralph: University of Wisconsin-Madison
Joseph S. M. Samec: Stockholm University
Feng Wang: Chinese Academy of Sciences

Nature, 2024, vol. 630, issue 8016, 381-386

Abstract: Abstract Lignocellulose is mainly composed of hydrophobic lignin and hydrophilic polysaccharide polymers, contributing to an indispensable carbon resource for green biorefineries1,2. When chemically treated, lignin is compromised owing to detrimental intra- and intermolecular crosslinking that hampers downstream process3,4. The current valorization paradigms aim to avoid the formation of new C–C bonds, referred to as condensation, by blocking or stabilizing the vulnerable moieties of lignin5–7. Although there have been efforts to enhance biomass utilization through the incorporation of phenolic additives8,9, exploiting lignin’s proclivity towards condensation remains unproven for valorizing both lignin and carbohydrates to high-value products. Here we leverage the proclivity by directing the C–C bond formation in a catalytic arylation pathway using lignin-derived phenols with high nucleophilicity. The selectively condensed lignin, isolated in near-quantitative yields while preserving its prominent cleavable β-ether units, can be unlocked in a tandem catalytic process involving aryl migration and transfer hydrogenation. Lignin in wood is thereby converted to benign bisphenols (34–48 wt%) that represent performance-advantaged replacements for their fossil-based counterparts. Delignified pulp from cellulose and xylose from xylan are co-produced for textile fibres and renewable chemicals. This condensation-driven strategy represents a key advancement complementary to other promising monophenol-oriented approaches targeting valuable platform chemicals and materials, thereby contributing to holistic biomass valorization.

Date: 2024
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DOI: 10.1038/s41586-024-07446-5

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