Universität zu Köln

Scott, Martin ORCID: 0000-0002-9830-3856, Sud, Abhishek, Boess, Esther and Klussmann, Martin ORCID: 0000-0002-9026-205X (2014). Reaction Progress Kinetic Analysis of a Copper-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline. J. Org. Chem., 79 (24). S. 12033 - 12041. WASHINGTON: AMER CHEMICAL SOC. ISSN 0022-3263

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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.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Scott, Martin UNSPECIFIED orcid.org/0000-0002-9830-3856 UNSPECIFIED Sud, Abhishek UNSPECIFIED UNSPECIFIED UNSPECIFIED Boess, Esther UNSPECIFIED UNSPECIFIED UNSPECIFIED Klussmann, Martin UNSPECIFIED orcid.org/0000-0002-9026-205X UNSPECIFIED
URN:	urn:nbn:de:hbz:38-420093
DOI:	10.1021/jo5018876
Journal or Publication Title:	J. Org. Chem.
Volume:	79
Number:	24
Page Range:	S. 12033 - 12041
Date:	2014
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	0022-3263
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language SP(3) C-H; CARBON-HYDROGEN BONDS; TERTIARY-AMINES; MOLECULAR-OXYGEN; POWERFUL METHODOLOGY; REACTION CALORIMETRY; ACID CATALYSIS; NITROGEN ATOM; FUNCTIONALIZATION; COMPLEXES Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/42009