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  Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol As a Solvent

Boess, E., Sureshkumar, D., Sud, A., Wirtz, C., Farès, C., & Klussmann, M. (2011). Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol As a Solvent. Journal of the American Chemical Society, 133(21), 8106-8109. doi:10.1021/ja201610c.

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ja201610c_si_001.pdf (Supplementary material), 3MB
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ja201610c_si_001.pdf
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 Creators:
Boess, Esther1, Author           
Sureshkumar, Devavajulu1, Author           
Sud, Abhishek1, Author           
Wirtz, Cornelia2, Author           
Farès, Christophe2, Author           
Klussmann, Martin1, Author           
Affiliations:
1Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445608              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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 Abstract: The mechanism of an aerobic copper-catalyzed oxidative coupling reaction with N-phenyl tetrahydroisoquinoline was investigated. The oxidized species formed from the reaction of the amine with the copper catalyst were analyzed by NMR-spectroscopy. An iminium dichlorocuprate was found to be the reactive intermediate and could be structurally characterized by X-ray crystallography. The effect of methanol to effectively stabilize the iminium ion was investigated and shown to be beneficial in an oxidative allylation reaction.

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Language(s): eng - English
 Dates: 2011-03-022011-05-112011-06-01
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/ja201610c
 Degree: -

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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 133 (21) Sequence Number: - Start / End Page: 8106 - 8109 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870