Deactivation of a ruthenium(II) N-heterocyclic carbene p-cymene complex during transfer hydrogenation catalysis |
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| Authors: | John R. Miecznikowski Nicholas A. Bernier Christopher A. Van Akin Sheila C. Bonitatibus Maura E. Morgan Rami M. Kharbouch Brandon Q. Mercado Matthew A. Lynn |
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| Affiliation: | 1.Department of Chemistry and Biochemistry,Fairfield University,Fairfield,USA;2.Department of Chemistry,Yale University,New Haven,USA;3.Department of Science and Mathematics,National Technical Institute for the Deaf, Rochester Institute of Technology,Rochester,USA;4.Department of Chemistry and Biochemistry,University of California, Los Angeles,Los Angeles,USA;5.University of Connecticut School of Medicine,Farmington,USA;6.Department of Chemistry,Boston University,Boston,USA |
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| Abstract: | A ruthenium (II) N-heterocyclic carbene (NHC) complex was synthesized to investigate ligand dissociation as a possible deactivation pathway for the catalytic cycle of a transfer hydrogenation reaction. Diiodo(1,3-dimethylbenzimidazole-2-ylidene)(p-cymene)ruthenium(II) was synthesized for use as the catalytic species and characterized using physico-chemical, spectroscopic methods, and single crystal X-ray diffraction. The transfer of hydrogen from isopropanol to acetophenone was followed using 1H NMR. We observed 94% conversion of the substrate to the alcohol product after 1 h. We also found that the p-cymene complex decomposed during the catalytic reaction to the extent of 80% deactivation after 1 h, based on 1H NMR spectrometry. From Gaussian calculations, an ultraviolet–visible spectrum that is in excellent agreement with the actual spectrum was computed, giving insight into the nature of the absorptions observed experimentally. |
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