Journal
SCIENTIFIC REPORTS
Volume 9, Issue -, Pages -Publisher
NATURE PORTFOLIO
DOI: 10.1038/s41598-019-47735-y
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- Ohio State University
- U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, Condensed Phase and Interfacial Molecular Science [DE-SC0016044]
- U.S. Department of Energy (DOE) [DE-SC0016044] Funding Source: U.S. Department of Energy (DOE)
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Visible-light mediated aerobic dehydrogenation of N-heterocyclic compounds is a reaction with enormous potential for application. Herein, we report the first complete aerobic dehydrogenation pathway to large-scale production of isoquinolines. The discovery of this visible light photoredox reaction was enabled through the combination of mathematical simulations and real-time quantitative mass spectrometry screening. The theoretical calculations showed that hyper-conjugation, the main underlying factor hindering the aerobic oxidation of tetrahydroisoquinolines, is relieved both by pi- and sigma-donating substituents. This mechanistic insight provided a novel photocatalytic route based on N-substituted auxiliaries that facilitated the conversion of tetrahydroisoquinolines into the corresponding isoquinolines in just three simple steps (yield 71.7% in bulk-solution phase), using unmodified Ru(bpy)(3)Cl-2 photocatalyst, sun energy, atmospheric O-2, and at ambient temperature.
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