Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction withN-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol As a Solvent
- 11 May 2011
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 133 (21) , 8106-8109
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.Keywords
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