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Investigating the Oxidation Step in the CuCl2-Catalyzed Aerobic Oxidative Coupling Reaction of N-Aryl Tetrahydroisoquinolines

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Boess,  Esther
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Van Hoof,  Max
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Birdsall,  Sarah Luna
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Klussmann,  Martin
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Boess, E., Van Hoof, M., Birdsall, S. L., & Klussmann, M. (2020). Investigating the Oxidation Step in the CuCl2-Catalyzed Aerobic Oxidative Coupling Reaction of N-Aryl Tetrahydroisoquinolines. The Journal of Organic Chemistry, 85(4), 1972-1980. doi:10.1021/acs.joc.9b02707.


Cite as: http://hdl.handle.net/21.11116/0000-0005-B12D-1
Abstract
The oxidative coupling of N-aryl tetrahydroisoquinolines with nucleophiles has inspired the development of novel C-H functionalization reactions as well as mechanistic studies. Here, we investigate the oxidation step that forms iminium ions as key intermediates in the method using CuCl2 as catalyst and oxygen as terminal oxidant. A strong electronic effect of substituents in the N-aryl ring was found by synthetic studies and a Hammett plot analysis, supporting initial electron transfer from the amine to Cu(II). The importance of the mechanism of oxidation on the substrate scope with differently substituted tetrahydroisoquinolines is discussed.