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Reaction Progress Kinetic Analysis of a Copper-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline

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

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

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

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Citation

Scott, M., Sud, A., Boess, E., & Klussmann, M. (2014). Reaction Progress Kinetic Analysis of a Copper-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline. The Journal of Organic Chemistry, 79(24), 12033-12040. doi:10.1021/jo5018876.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0024-C2D6-C
Abstract
The results from a kinetic investigation of a Cu-catalyzed oxidative coupling reaction between N-phenyl tetrahydroisoquinoline and a silyl enol ether using elemental oxygen as oxidant are presented. By using reaction progress kinetic analysis as an evaluation method for the obtained data, we discovered information regarding the reaction order of the substrates and catalysts. Based on this information and some additional experiments, a refined model for the initial oxidative activation of the amine substrate and the activation of the nucleophile by the catalyst was developed. The mechanistic information also helped to understand why silyl nucleophiles have previously failed in a related Cu-catalyzed reaction using tert-butyl hydroperoxide as oxidant and how to overcome this limitation.