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Efficient Ruthenium-Catalyzed Aerobic Oxidation of Alcohols Using a Biomimetic Coupled Catalytic System
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2002 In: Journal of Organic Chemistry, ISSN 0022-3263, Vol. 67, no 5, 1657-1662 p.Article in journal (Refereed) Published
Place, publisher, year, edition, pages
2002. Vol. 67, no 5, 1657-1662 p.
Identifiers
URN: urn:nbn:se:su:diva-24476OAI: oai:DiVA.org:su-24476DiVA: diva2:197625
Note
Part of urn:nbn:se:su:diva-71Available from: 2004-03-11 Created: 2004-03-11Bibliographically approved
In thesis
1. Studies of Biomimtic Oxidations and Racemizations
Open this publication in new window or tab >>Studies of Biomimtic Oxidations and Racemizations
2004 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis deals with studies of ruthenium-catalyzed hydrogen transfer reactions for oxidations and racemization.

Through optimisation of the substrate-selective redox catalyst, the electron and proton transfer mediator (a benzoquinone derivative), and the oxygen-activating metal macrocycle a highly efficient biomimetic oxidation of secondary alcohols was obtained. Several alcohols were subjected to the new oxidation protocol and the corresponding ketones were isolated in high yield.

The deactivation of the oxygen-activating metal macrocycle retarded the aerobic oxidation of primary alcohols. Encapsulation of the metal macrocycle into zeolite, described in chapter 3, proved to be an efficient method to solve this problem and comparable conversion of alcohols was achieved. The immobilization of the oxygen-activating porphyrin to a surface can be an alternative approach to solve the deactivation problem. Therefore as the first step towards studies of immobilized porphyrins on a metal surface (of gold or silver), S-thioacetyl derivatized porphyrins were synthesized; two alternative syntheses are described in chapter 4.

A new and effecient ruthenium-catalyzed racemization protocol was established by proper ligand tuning. The racemization of the enantiomerically pure alcohols was increased significantly; this work is reported in chapter 5.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2004. 52 p.
Keyword
oxidation of alcohols, ruthenium, porphyrin, racemization
National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-71 (URN)91-7265-819-3 (ISBN)
Public defence
2004-04-01, Magnélisalen, Arrheniuslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
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Available from: 2004-03-11 Created: 2004-03-11 Last updated: 2013-08-15Bibliographically approved

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