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Palladium-catalyzed Allylic C-H and C-OH Functionalization. Reactions of the Obtained Allylboronic Acids
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2014 (English)Licentiate thesis, monograph (Other academic)
Abstract [en]

This thesis is focused on the studies of two major transformations. The first transformation deals with the development of palladium-catalyzed selective allylic trifluoroacetoxylation reactions based on C-H functionalization, whereas the second comprises the synthesis and isolation of allylboronic acids using diboronic acid B2(OH)4 as boron source. Both reactions proceed with a very high regio- and stereoselectivity. The mechanistic studies of the allylic C-H trifluoroacetoxylation indicate that the reaction proceeds via (η3-allyl)palladium intermediate.

The reactivity of the allylboronic acids was studied with ketone and imine substrates. Unlikeother boronates (such as allyl-Bpin derivatives), allylboronic acids react with ketones and imines without any additives under neutral and mild conditions (typically at room temperature). The regio- and stereoselectivity of this reaction is remarkably high. Using functionalized allylboronic acids (prepared in the above mentioned Pd-catalyzed reactions) homoallylic alcohols and amines with adjacent tertiary and quaternary centers could be obtained with high selectivity. Interestingly, both the ketones and the imines reacted with anti-stereoselectivity. This was surprising for the imines. Our mechanistic study has shown that the acyclic aldimines undergo cis/trans isomerization prior to the allylation reaction.

Place, publisher, year, edition, pages
Stockholm: Stockholms universitets förlag, 2014. , 35 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-104083OAI: oai:DiVA.org:su-104083DiVA: diva2:720518
Presentation
2014-06-18, room A501/507, Arrheniuslaboratoriet, Svante Arrheniusväg 16C, Stockholm, 11:00 (English)
Available from: 2014-05-30 Created: 2014-05-30 Last updated: 2014-07-22Bibliographically approved

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