For valorization of biomass, the conversion of lignin to deoxygenated bulk aromatic compounds is an emerging subject of interest. Because aromatic rings are susceptible to metal-catalysed hydrogenation, the selective hydrogenolysis of carbon-oxygen bonds still remains a great challenge. Herein we report direct and selective hydrogenolysis of sp(2) C-OH bonds in substituted phenols and naphthols catalysed by hydroxycyclopentadienyl iridium complexes. The corresponding arenes were obtained in up to 99% yields, indicating the possible production of arenes from lignin-derived bio-oils. Furthermore, the same catalysts were applied to the unprecedented selective hydrogenolysis of the sp(3) C-O bonds in aryl methyl ethers. Thus, the hydrodeoxygenation of vanillylacetone, a lignin model compound, afforded alkylbenzenes as the major products via triple deoxygenation.
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