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Iridium-Catalyzed Enantio- and Diastereoselective Hydrogenation of Acyclic Tetra-Substituted Olefins
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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(English)Manuscript (preprint) (Other academic)
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-152346OAI: oai:DiVA.org:su-152346DiVA, id: diva2:1179258
Available from: 2018-01-31 Created: 2018-01-31 Last updated: 2018-04-16Bibliographically approved
In thesis
1. NHC,P- and N,P-Iridium Catalysts for Hydrogenations and Hydrogen Transfer Reactions
Open this publication in new window or tab >>NHC,P- and N,P-Iridium Catalysts for Hydrogenations and Hydrogen Transfer Reactions
2018 (English)Doctoral thesis, comprehensive summary (Other academic)
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.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2018
Keywords
Iridium catalyst, carbene, N, P-ligand, asymmetric hydrogenation, alkylation, hydrogen transfer reaction
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-152341 (URN)978-91-7797-120-7 (ISBN)978-91-7797-121-4 (ISBN)
Public defence
2018-03-16, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (English)
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Supervisors
Note

At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 3: Manuscript. Paper 4: Manuscript.

Available from: 2018-02-21 Created: 2018-01-31 Last updated: 2018-04-16Bibliographically approved

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