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Palladium-Catalyzed Selective Acyloxylation Using Sodium Perborate as Oxidant
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2011 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 76, no 5, 1503-1506 p.Article in journal (Refereed) Published
Abstract [en]

Sodium perborate (SPB), a principal component of washing powders, was employed as an inexpensive and eco-friendly oxidant in the palladium-catalyzed C-H acyloxylation of alkenes in excellent regio- and stereochemistry. The reactions used anhydrides as acyloxy sources. The method applies to both terminal and internal alkenes, and even benzylic C-H oxidation.

Place, publisher, year, edition, pages
2011. Vol. 76, no 5, 1503-1506 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-69434DOI: 10.1021/jo1024199ISI: 000287636200041OAI: oai:DiVA.org:su-69434DiVA: diva2:478232
Note
authorCount :3Available from: 2012-01-16 Created: 2012-01-12 Last updated: 2017-12-08Bibliographically approved
In thesis
1. Oxidative Trifluoromethylation and other Functionalization Reactions of Alkenes and Alkynes
Open this publication in new window or tab >>Oxidative Trifluoromethylation and other Functionalization Reactions of Alkenes and Alkynes
2014 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis concerns the use of various potent oxidants in organic synthesis. The main focus is directed at selectively introducing trifluoromethyl groups into compounds containing double or triple bonds. All reactions proceed under mild conditions and can in most cases be performed on the bench-top.

We have developed three different procedures for transformations of activated alkenes and alkynes as well as quinones. In paper I the selective introduction of a trifluoromethyl group together with an oxygen functionality to double and triple bonds is demonstrated.

Paper II is focused on the related chemoselective cyanotrifluoromethylation in which a cyano group is added instead of the oxygen functionality.

Paper III describes a new procedure for C–H trifluoromethylation of quinones. Our studies on the mechanistic aspects of the above reactions are described in Paper IV. In these studies we investigated the ligand and substituent effects in Cu-catalyzed reactions.

Paper V is focused on a conceptually new palladium-catalyzed allylic C–H acyloxylation of olefins under oxidative conditions. The procedure uses an inexpensive, safe and environmentally benign oxidant, sodium perborate, which is activated with acetic anhydride.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2014. 63 p.
Keyword
palladium, copper, transition metal, trifluoromethylation, catalysis, acetoxylation, difunctionalization, oxidation, mechanistic study, alkenes, alkynes, quinones
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-103064 (URN)978-91-7447-930-0 (ISBN)
Public defence
2014-06-05, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 13:00 (English)
Opponent
Supervisors
Note

At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 4: Submitted.

Available from: 2014-05-14 Created: 2014-04-30 Last updated: 2017-01-02Bibliographically approved

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