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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Authors: | Boess Esther Sureshkumar Devarajulu Sud Abhishek Wirtz Cornelia Farès Christophe Klussmann Martin |
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Institution: | Max-Planck-Institut fu?r Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mu?lheim an der Ruhr, Germany. |
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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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