Efficient ruthenium-catalyzed hydrogenation of aromatic dicarboxylates supported by a 1-phenylethylamine-based P,N,N-ligand

Abstract

The ruthenium-catalyzed hydrogenation of aromatic dicarboxylates supported by a 1-phenylethylamine-derived P,N,N-pincer ligand has been developed. The newly developed catalytic system displayed high efficiency to the hydrogenation of aromatic dicarboxylates with broad substrate scope and high functional group tolerance. The hydrogenation led to the formation of a variety of 1,2-, 1,3- and 1,4-benzenedimethanols as well as heteroaromatic dimethanols in good to high yields. The synthetic utility of the hydrogenation is highlighted by a gram-scale preparation of 1,4-benzenedimethanol at a low catalyst loading and the synthesis of pyrethroid hygienic insecticide heptafluthrin.