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Hashemi Hosseini, Behdokht, 2026, "Metal-Free Sonophotocatalytic C–C Coupling of Acetovanillone Using a Synthesis-Frequency-Tuned Chitosan–Lignin Hybrid Catalyst", https://doi.org/10.18150/3XQLVG, RepOD, V1
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A metal-free sonophotocatalytic system based on a biopolymer-derived hybrid catalyst is reported for the selective C–C coupling of lignin-derived acetovanillone to the pharmaceutically relevant dimer diapocynin. The system employs a frequency-optimized chitosan–lignin (CL) sonophotocatalyst (Syn-340) under synergistic 365 nm UV-A irradiation (∼300 W m–2) and high-frequency ultrasound (500 kHz), affording diapocynin in 33% yield with >97% selectivity at ambient temperature and pressure after 15 h. The lower photon energy of UV-A relative to UV-C suppresses non-selective substrate photolysis, thereby preserving the >97% C–C selectivity. Selective excitation suppresses over-oxidation of phenoxyl radicals to phenoxenium ions, preventing ring opening and mineralization. The high primary amine density of Syn-340 promotes single-electron oxidation. The radical mechanism was confirmed by TEMPO inhibition, while scavenger tests identified •OH and O2•⁻ as the dominant reactive species, with h+ contributing least. A mechanistic investigation combining acoustic pressure mapping, time-resolved mass spectrometry, and luminol imaging reveals a frequency-dependent trade-off between reactive species generation and cavitation stability. Although 500 kHz enables the reaction, 22 kHz provides greater stability and reproducibility for future optimization. This work demonstrates a metal-free route to lignin-derived acetovanillone and offers design insights for future lignin valorization using biopolymer-based sonophotocatalysts.
Acetovanillone, Biomass, C–C Coupling, Diapocynin, Photocatalysis, Radical Reactions, Sonocatalysis, Sono-Photocatalysis, Sustainable Chemistry
CC BY - Creative Commons Attribution 4.0
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