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Iridium-Catalyzed Enantio- and Diastereoselective Hydrogenation of Acyclic Tetra-Substituted Olefins
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Vise andre og tillknytning
(engelsk)Manuskript (preprint) (Annet vitenskapelig)
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-152346OAI: oai:DiVA.org:su-152346DiVA, id: diva2:1179258
Tilgjengelig fra: 2018-01-31 Laget: 2018-01-31 Sist oppdatert: 2019-12-04bibliografisk kontrollert
Inngår i avhandling
1. NHC,P- and N,P-Iridium Catalysts for Hydrogenations and Hydrogen Transfer Reactions
Åpne denne publikasjonen i ny fane eller vindu >>NHC,P- and N,P-Iridium Catalysts for Hydrogenations and Hydrogen Transfer Reactions
2018 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The work described in this thesis is focused on hydrogenation and hydrogen transfer reactions using iridium catalysts. The first part concerns the use of N-heterocyclic carbene-phosphine iridium complexes in alkylation reactions (Chapters 2 and 3) and the hydrogenation of ketones (Chapter 4). A number of N-heterocyclic carbene-phosphine iridium complexes have been prepared and evaluated as catalysts for C-N bond formation of amides using alcohols as the electrophile. This catalytic system can be used with a wide range of substrates at low catalyst loading (only 0.5 mol%) to furnish the desired products in up to 98% isolated yield. The achiral N-heterocyclic carbene-phosphine iridium complexes were also found to catalyze the methylation of ketones with methanol under mild conditions to afford the mono-methylated products in up to 98% isolated yield with low catalyst loading (1.0 mol%). Additionally, several chiral N-heterocyclic carbene-phosphine iridium complexes were synthesized and evaluated in asymmetric hydrogenation of ketones. The reactions were carried out at room temperature under base-free conditions to obtain the chiral alcohols in up to 96% ee in 30 minutes.

The second part of this thesis (Chapter 5) details the preparation of new N,P-iridium complexes which were found to be highly efficient catalysts for the asymmetric hydrogenation of challenging tetrasubstituted olefins. This catalytic system results in optically active compounds of high enantiomeric excess (up to 98% ee) as the single diasteroisomer.

sted, utgiver, år, opplag, sider
Stockholm: Department of Organic Chemistry, Stockholm University, 2018
Emneord
Iridium catalyst, carbene, N, P-ligand, asymmetric hydrogenation, alkylation, hydrogen transfer reaction
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-152341 (URN)978-91-7797-120-7 (ISBN)978-91-7797-121-4 (ISBN)
Disputas
2018-03-16, 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 3: Manuscript. Paper 4: Manuscript.

Tilgjengelig fra: 2018-02-21 Laget: 2018-01-31 Sist oppdatert: 2018-04-16bibliografisk kontrollert

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