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

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.

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 Creators:
Scott, Martin1, Author
Sud, Abhishek2, Author              
Boess, Esther2, Author              
Klussmann, Martin2, Author              
Affiliations:
1Department of Chemistry, Cologne University, ou_persistent22              
2Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445608              

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 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.

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Language(s): eng - English
 Dates: 2014-08-152014-09-092014-09-092014-12-19
 Publication Status: Published in print
 Pages: 8
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jo5018876
 Degree: -

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Title: The Journal of Organic Chemistry
  Other : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 79 (24) Sequence Number: - Start / End Page: 12033 - 12040 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1