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American Chemical Society, ACS Catalysis, 2(6), p. 1247-1253, 2016

DOI: 10.1021/acscatal.5b02638

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A ruthenium catalyst with unprecedented effectiveness for the coupling cyclization of $γ$-amino alcohols and secondary alcohols

Journal article published in 2016 by Bing Pan, Bo Liu, Erlin Yue, Qingbin Liu, Xinzheng Yang, Zheng Wang ORCID, Wen-Hua Sun
This paper is available in a repository.
This paper is available in a repository.

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Abstract

The ruthenium complex, (8-(2-diphenylphosphinoethyl)aminotrihydroquinolinyl) (carbonyl)(hydrido)ruthenium chloride, exhibited extremely high efficiency toward the coupling cyclization of -aminoalcohols 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 γ-aminoalcohols reached 0.5 – 1.0 mol% for Ru and the lowest record 0.04 mol% for Ir, the current catalyst achieves the same efficiency with a loading of 0.025 mol% Ru. The mechanism of acceptorless dehydrogenative condensation (ADC) was proposed on the basis of the DFT calculations; meanwhile the reactive intermediates were determined by GC-MS, NMR and single crystal X-ray diffraction. The catalytic process is potentially suitable for industrial application.