The upgrading of lignin is a sustainable and promising pathway for fossil-based aromatic compounds but always faces low selectivity. Herein, a metal-free photocatalyst, 2,4,6-triphenylpyrylium tetrafluoroborate (TPP), was illustrated to remarkably facilitate the regioselective oxidative C-C bond cleavage of β-1 and β-O-4 lignin alcohol/ketone models into aromatic acids (92-99% yields) under visible-light irradiation at room temperature without any additive/co-catalyst, which was enabled by the synergistic effect of C-H⋯C(TPP) interaction and·˙O/O species. The synergy of the catalyst-substrate interaction and active species offers a reference for the enhancive and selective transformation of polymeric biomass and complex molecules.
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