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Efficient Ruthenium-Catalyzed Transfer Hydrogenation of Functionalized Imines by Isopropanol under Controlled Microwave Heating
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2005 (English)In: Canadian journal of chemistry (Print), ISSN 0008-4042, E-ISSN 1480-3291, Vol. 83, no 6, 909-916 p.Article in journal (Refereed) Published
Abstract [en]

Transfer hydrogenation of various functionalized imines by isopropanol catalyzed by [Ru(CO)(2)(Ph4C4CO)](2) (3) has been studied. The use of either an oil bath or controlled microwave heating in toluene led to an efficient procedure with high turnover frequencies and the product amines were obtained in high yields. An advantage with catalyst 3 over the conventional [Ru-2(CO)(4)(mu-H)(Ph4C4COHOCC4Ph4)] (1) is the absence of an initiation period, which results in a faster reaction with 3 as compared to 1.

Place, publisher, year, edition, pages
2005. Vol. 83, no 6, 909-916 p.
Keyword [en]
transfer hydrogenation, ruthenium, imines, microwave
National Category
Other Basic Medicine
URN: urn:nbn:se:su:diva-23688DOI: 10.1139/V05-103OAI: diva2:193993
Available from: 2005-04-07 Created: 2005-04-07 Last updated: 2010-10-29Bibliographically 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
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
Available from: 2005-04-07 Created: 2005-04-07Bibliographically approved

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Bäckvall, Jan-E
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