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

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.

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 Creators:
Boess, Esther1, Author           
Van Hoof, Max1, Author           
Birdsall, Sarah Luna1, Author           
Klussmann, Martin1, Author           
Affiliations:
1Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445608              

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 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.

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Language(s): eng - English
 Dates: 2019-10-072019-12-132020-02-21
 Publication Status: Published in print
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.joc.9b02707
 Degree: -

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Title: The Journal of Organic Chemistry
  Other : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 85 (4) Sequence Number: - Start / End Page: 1972 - 1980 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1