A Ruthenium Catalyst with Unprecedented Effectiveness for the Coupling Cyclization of γ-Amino Alcohols and Secondary Alcohols

The ruthenium complex (8-(2-diphenylphosphinoethyl)aminotrihydroquinolinyl) (carbonyl) (hydrido)ruthenium chloride exhibited extremely high efficiency toward the coupling cyclization of gamma-amino alcohols with secondary alcohols. The corresponding products, pyridine or quinoline derivatives, are obtained in good to high isolated yields. On comparison with literature catalysts whose noble-metal loading with respect to gamma-amino alcohols reached 0.5-1.0 mol % for Ru and a record lowest of 0.04 mol % for It, the current catalyst achieves the same efficiency with a loading of 0.025 mol % for Ru. The mechanism of acceptorless dehydrogenative condensation (ADC) was proposed on the basis of DFT calculations; in addition, the reactive intermediates were determined by GC-MS, NMR, and single-crystal X-ray diffraction. The catalytic process is potentially suitable for industrial applications.