English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

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

MPS-Authors
/persons/resource/persons58448

Boess,  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;

Fulltext (restricted access)
There are currently no full texts shared for your IP range.
Fulltext (public)
There are no public fulltexts stored in PuRe
Supplementary Material (public)

ja201610c_si_001.pdf
(Supplementary material), 3MB

Citation

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.


Cite as: http://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.