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Direct synthesis of functionalized allylic boronic esters from allylic alcohols and inexpensive reagents and catalysts
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
2008 (Engelska)Ingår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, nr 14, s. 2293-2297Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

A remarkably simple and effective system for the direct conversion of allylic alcohols into high value allylic boronic esters using commercially available reagents and catalysts is described.

Ort, förlag, år, upplaga, sidor
2008. nr 14, s. 2293-2297
Nyckelord [en]
allylation, palladium, palladacycles, transition metal
Identifikatorer
URN: urn:nbn:se:su:diva-14906DOI: 10.1055/s-2008-1067144ISI: 000258224600021OAI: oai:DiVA.org:su-14906DiVA, id: diva2:181426
Tillgänglig från: 2008-12-03 Skapad: 2008-12-03 Senast uppdaterad: 2017-12-13Bibliografiskt granskad
Ingår i avhandling
1. Catalytic Functionalization of Allylic Substrates by Palladium Pincer Complexes
Öppna denna publikation i ny flik eller fönster >>Catalytic Functionalization of Allylic Substrates by Palladium Pincer Complexes
2010 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Stockholm: Department of Organic Chemistry, Stockholm University, 2010. s. 65
Nyckelord
Catalysis, Palladium, Pincer Complex, Boron, Multicomponent Reaction
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-39065 (URN)978-91-7447-090-1 (ISBN)
Disputation
2010-06-22, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 13:00 (Engelska)
Opponent
Handledare
Anmärkning
At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 11: In press.Tillgänglig från: 2010-05-24 Skapad: 2010-05-06 Senast uppdaterad: 2010-05-21Bibliografiskt granskad

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Selander, NicklasSzabó, Kálmán J.
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Institutionen för organisk kemi
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Synthesis (Stuttgart)

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