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Performance of SCS palladium pincer complexes in borylation of allylic alcohols. Control of the regioselectivity in the one-pot borylation-allylation process
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0002-9349-7137
2009 (engelsk)Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 74, nr 15, s. 5695-5698Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

One-pot borylation−allylation reactions of aldehydes and allylic alcohols were performed under various reaction conditions. The borylation of allylic alcohols was performed using a very efficient SCS palladium pincer-complex catalyst. The regioselectivity of the allylation depends on the applied solvent. The reaction in CHCl3 gave the linear allylic product; however, when MeOH was added to the reaction mixture, the branched allylic product was formed.

sted, utgiver, år, opplag, sider
American Chemical Society , 2009. Vol. 74, nr 15, s. 5695-5698
HSV kategori
Identifikatorer
URN: urn:nbn:se:su:diva-31751DOI: 10.1021/jo9008673ISI: 000268480300090OAI: oai:DiVA.org:su-31751DiVA, id: diva2:278464
Tilgjengelig fra: 2009-11-26 Laget: 2009-11-26 Sist oppdatert: 2019-12-16bibliografisk kontrollert
Inngår i avhandling
1. Catalytic Functionalization of Allylic Substrates by Palladium Pincer Complexes
Åpne denne publikasjonen i ny fane eller vindu >>Catalytic Functionalization of Allylic Substrates by Palladium Pincer Complexes
2010 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Stockholm: Department of Organic Chemistry, Stockholm University, 2010. s. 65
Emneord
Catalysis, Palladium, Pincer Complex, Boron, Multicomponent Reaction
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-39065 (URN)978-91-7447-090-1 (ISBN)
Disputas
2010-06-22, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 13:00 (engelsk)
Opponent
Veileder
Merknad
At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 11: In press.Tilgjengelig fra: 2010-05-24 Laget: 2010-05-06 Sist oppdatert: 2010-05-21bibliografisk kontrollert

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