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Evaluation of Fe and Ru Pincer-Type Complexes as Catalysts for the Racemization of Secondary Benzylic Alcohols
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Universität Rostock, Germany.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Vise andre og tillknytning
2016 (engelsk)Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, nr 33, s. 11583-11586Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Fe and Ru pincer-type catalysts are used for the racemization of benzylic alcohols. Racemization with the Fe catalyst was achieved within 30 minutes under mild reaction conditions, with a catalyst loading as low as 2 mol %. This reaction constitutes the first example of an iron-catalyzed racemization of an alcohol. The efficiency for racemization of the Fe catalyst and its Ru analogue was evaluated for a wide range of sec-benzylic alcohols. The commercially available Ru complex proved to be highly robust and even tolerated the presence of water in the reaction mixture.

sted, utgiver, år, opplag, sider
Wiley-VCH Verlagsgesellschaft, 2016. Vol. 22, nr 33, s. 11583-11586
Emneord [en]
iron, pincer ligands, racemization, ruthenium, secondary alcohols
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-135116DOI: 10.1002/chem.201601793ISI: 000382921600015PubMedID: 27311070OAI: oai:DiVA.org:su-135116DiVA, id: diva2:1044524
Forskningsfinansiär
Swedish Research CouncilEU, European Research CouncilBerzelii Centre EXSELENTKnut and Alice Wallenberg FoundationTilgjengelig fra: 2016-11-03 Laget: 2016-10-31 Sist oppdatert: 2018-11-08bibliografisk kontrollert
Inngår i avhandling
1. Studies on Metalloenzymatic Dynamic Kinetic Resolutions and Iron-Catalyzed Reactions of Allenes
Åpne denne publikasjonen i ny fane eller vindu >>Studies on Metalloenzymatic Dynamic Kinetic Resolutions and Iron-Catalyzed Reactions of Allenes
2018 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The main focus of this thesis lies in the development of new transition metal-catalyzed chemoenzymatic dynamic kinetic resolutions (DKR) of both alcohols and amines. The first part of the thesis deals with the development of new heterogeneous systems for the DKR of amines. The racemization catalysts in these different systems are all composed of palladium nanoparticles supported on either mesoporous silica or incorporated in a biocomposite that is composed of a bioactive cross-linked enzyme aggregate. 

The second part of the thesis deals with the development of a homogeneous iron catalyst in the racemization of sec-alcohols for the implementation in a chemoenzymatic DKR. Two protocols for the racemization of sec-alcohols are reported. The first one could not be combined with a chemoenzymatic kinetic resolution, although this was overcome in the second iron based protocol. 

Following the successful iron catalyzed chemoenzymatic DKR of sec-alcohols, the iron catalyst was used in the cyclization of α-allenic alcohols and N-protected amines to furnish 2,3-dihydrofurans and 2,3-dihydropyrroles, respectively. The cyclization is proceeding in a diastereoselective manner.

The last part of the thesis deals with attempts to further elucidate the mechanism of activation of a known ruthenium racemization catalyst. X-ray absorption spectroscopy using synchrotron radiation was used for this purpose.

sted, utgiver, år, opplag, sider
Stockholm: Department of Organic Chemistry, Stockholm University, 2018. s. 97
Emneord
Racemization, Dynamic Kinetic Resolution, Enzyme Catalysis, XAS, Asymmetric Synthesis
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-153952 (URN)978-91-7797-195-5 (ISBN)978-91-7797-196-2 (ISBN)
Disputas
2018-04-27, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (engelsk)
Opponent
Veileder
Merknad

At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 4: Manuscript. Paper 7: Manuscript. Paper 8: Manuscript.

Tilgjengelig fra: 2018-04-04 Laget: 2018-03-09 Sist oppdatert: 2018-03-22bibliografisk kontrollert

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