title: 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.
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.
authors.affiliation: Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.
authors.forename: Esther
authors.initials: E
authors.lastname: Boess
authors.forename: Devarajulu
authors.initials: D
authors.lastname: Sureshkumar
authors.forename: Abhishek
authors.initials: A
authors.lastname: Sud
authors.forename: Cornelia
authors.initials: C
authors.lastname: Wirtz
authors.forename: Christophe
authors.initials: C
authors.lastname: Farès
authors.forename: Martin
authors.initials: M
authors.lastname: Klussmann