Selective route to 2-propenyl aryls directly from wood by a tandem organosolv and palladium-catalysed transfer hydrogenolysis

Abstract

A tandem organosolv pulping and Pd-catalysed transfer hydrogenolysis depolymerisation and deoxygenation has been developed. The tandem process generated 2-methoxy-4-(prop-1-enyl)phenol in 23% yield (92% theoretical monomer yield) starting from pine wood and 2,6-dimethoxy-4-(prop-1-enyl)phenol in 49% yield (92% theoretical monomer yield) starting from birch wood. Only endogenous hydrogen from wood was consumed, and the reaction was performed using green solvents.

Keywords: biomass; cleavage reactions; heterogeneous catalysis; hydrogen; palladium.