Oxidative Trifluoromethylation and other Functionalization Reactions of Alkenes and Alkynes
2014 (English)Doctoral thesis, comprehensive summary (Other academic)
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.
palladium, copper, transition metal, trifluoromethylation, catalysis, acetoxylation, difunctionalization, oxidation, mechanistic study, alkenes, alkynes, quinones
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-103064ISBN: 978-91-7447-930-0OAI: oai:DiVA.org:su-103064DiVA: diva2:715347
2014-06-05, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 13:00 (English)
Togni, Antonio, Professor
Szabó, Kálmán, Professor
At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 4: Submitted.2014-05-142014-04-302014-05-14Bibliographically approved
List of papers