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Highly Selective and Robust Palladium-Catalysed Carbon-Carbon Coupling between Allyl Alcohols and Aldehydes via Transient Allylboronic Acids
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Prof. Kálmán J. Szabó)
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Prof. Kálmán J. Szabó)
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Prof. Kálmán J. Szabó)
(Prof. Kálmán J. Szabó)
2006 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 18, 4085-4087 p.Article in journal (Refereed) Published
Abstract [en]

The highly regio- and stereoselective coupling of allyl alcohols with aldehydes could be achieved with 5 mol-% of SeCSe pincer complex catalyst and p-toluenesulfonic acid in the presence of diboronic acid. The transformations have a broad synthetic scope, and the high yields were obtained without the use of an inert atmosphere and carefully dried solvents.

Place, publisher, year, edition, pages
Weinheim: WILEY-VCH , 2006. no 18, 4085-4087 p.
Keyword [en]
Aldehydes, Allylation, Boron, Electrophilic substitution, Palladium
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-39078DOI: 10.1002/ejoc.200600530OAI: oai:DiVA.org:su-39078DiVA: diva2:318326
Available from: 2010-05-07 Created: 2010-05-07 Last updated: 2017-12-12Bibliographically 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.
Keyword
Catalysis, Palladium, Pincer Complex, Boron, Multicomponent Reaction
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
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)
Opponent
Supervisors
Note
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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