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Synthesis of stereodefined substituted cycloalkenes by a one-pot catalytic boronation-allylation-metathesis sequence
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2008 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 350, no 13, 2045-2051 p.Article in journal (Refereed) Published
Abstract [en]

Stereodefined cyclohexene and cyclopentene derivatives were prepared by the coupling of allylic alcohols and other allylic precursors with unsaturated aldehydes. These reactions are based on a multicatalytic one-pot approach involving palladium pincer complex-catalyzed boronation, allylation and ring-closing metathesis reactions. This reaction sequence can be performed in an operationally simple procedure affording the cycloalkene products in high overall yields and excellent regio- and stereoselectivities. The presented procedure has a broad synthetic scope and high functional group tolerance, which allows the synthesis of bicyclic lactone and spirane skeletons and various substitution patterns including hydroxy, silyl, vinyl, allyl, and sulfonyl groups. The studied catalytic one-pot reactions involve up to three individual processes performed by up to four acid- and transition metal-catalyzed events.

Place, publisher, year, edition, pages
2008. Vol. 350, no 13, 2045-2051 p.
Keyword [en]
allylation, boronation, homogenous catalysis, metathesis, palladium pincer complexes, stereoselectivity
URN: urn:nbn:se:su:diva-14905DOI: 10.1002/adsc.200800324ISI: 000259544300020OAI: diva2:181425
Available from: 2009-01-02 Created: 2009-01-02 Last updated: 2010-05-21Bibliographically approved
In thesis
1. Catalytic Functionalization of Allylic Substrates by Palladium Pincer Complexes
Open this publication in new window or tab >>Catalytic Functionalization of Allylic Substrates by Palladium Pincer Complexes
2010 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis is based on the development of novel catalytic reactions for the synthesis and application of organometallic reagents. The main focus is directed towards organoboronate derivatives. We developed an efficient procedure for converting allylic alcohols to the corresponding allylboronates using palladium pincer complexes as catalysts. The reactions were performed under mild conditions with high selectivity, allowing further one-pot transformations. Using this approach, a variety of stereodefined homoallylic alcohols and amino acid derivatives were synthesized via trapping of the in situ generated allylboronate derivatives with an appropriate electrophile. The synthetic scope of these types of multi-component reactions is broad as many different substrate allylic alcohols may be used together with various electrophiles. Several aspects of these reactions were studied, including different reagents, catalysts and electrophiles.

Furthermore, we studied the possibility to use oxidizing reagents as an essential component in the functionalization of olefins. Two main strategies were utilized for these catalytic methods using palladium pincer complexes. The functional group was either transferred from the oxidizing reagent, or introduced via an oxidation-transmetallation route. We propose that both methods involve palladium(IV) intermediates thus expanding both the coordination sphere of palladium and the synthetic scope of pincer complex catalysis.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2010. 65 p.
Catalysis, Palladium, Pincer Complex, Boron, Multicomponent Reaction
National Category
Organic Chemistry
Research subject
Organic Chemistry
urn:nbn:se:su:diva-39065 (URN)978-91-7447-090-1 (ISBN)
Public defence
2010-06-22, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 13:00 (English)
At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 11: In press.Available from: 2010-05-24 Created: 2010-05-06 Last updated: 2010-05-21Bibliographically approved

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Selander, NicklasSzabó, Kálmán J.
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