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

Böß, Esther; Sureshkumar, Devavajulu; Sud, Abhishek; Wirtz, Cornelia; Farès, Christophe; Klussmann, Martin

doi:10.1021/ja201610c

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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

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

/persons/resource/persons59031

Sureshkumar, Devavajulu
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons59028

Sud, Abhishek
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons59119

Wirtz, Cornelia
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58537

Farès, Christophe
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58702

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

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http://pubs.acs.org/doi/suppl/10.1021/ja201610c/suppl_file/ja201610c_si_003.cif
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Citation

Böß, 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.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-CA39-4

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.