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Efficient Ruthenium-Catalyzed Aerobic Oxidation of Amines Using a Biomimetic Coupled Catalytic System
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2005 In: Chemistry : a European journal, ISSN 0947-6539, Vol. 11, no 8, 2327-2334 p.Article in journal (Refereed) Published
Place, publisher, year, edition, pages
2005. Vol. 11, no 8, 2327-2334 p.
Identifiers
URN: urn:nbn:se:su:diva-23690OAI: oai:DiVA.org:su-23690DiVA: diva2:193995
Note
Part of urn:nbn:se:su:diva-447Available from: 2005-04-07 Created: 2005-04-07Bibliographically approved
In thesis
1. Ruthenium-catalyzed hydrogen transfer involving amines and imines: Mechanistic studies and synthetic applications
Open this publication in new window or tab >>Ruthenium-catalyzed hydrogen transfer involving amines and imines: Mechanistic studies and synthetic applications
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis deals with ruthenium-catalyzed hydrogen transfer involving amines and imines and is divided into two parts.

In Part 1 a mechanistic study has been performed. The complexation of the imine to the catalyst and the decomplexation patterns of the formed ruthenium-amine complexes, isotope studies, and exchange studies show that the mechanism of the hydrogen transfer involving amines and imines is different from the hydrogen transfer involving alcohols and carbonyls.

In Part 2 synthetic applications of the hydrogen transfer is presented. First the rutheniumcatalyzed transfer hydrogenation of imines by 2-propanol in an unpolar solvent was investigated. The corresponding amines were isolated in good to excellent yields. Even imines bearing labile functional groups were smoothly transferred to amines with very low catalyst loadings and short reaction times employing microwave heating. Then the reverse reaction, transfer dehydrogenation of amines to imines, was investigated using either MnO2 or oxygen as terminal oxidant. Important products such as aldimines, ketimines, and non benzylic anilines were prepared in the aerobic oxidation. We also demonstrated that the aerobic oxidation is compatible with proline-mediated organocatalysis, yielding amines in high yields and ee:s. Finally the racemization of chiral amines was investigated. A cumbersome side product formation was investigated and hampered by the use of a mild hydrogen donor, giving a mild and efficient racemization process for both primary and secondary amines.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2005. 44 p.
National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-447 (URN)91-7155-041-0 (ISBN)
Public defence
2005-04-29, De Geersalen, Geovetenskapens hus, Svante Arrhenius väg 8 A, Stockholm, 14:00
Opponent
Supervisors
Available from: 2005-04-07 Created: 2005-04-07Bibliographically approved

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