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C-N Coupling of Amides with Alcohols Catalyzed by N-Heterocyclic Carbene-Phosphine Iridium Complexes
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0002-6053-8828
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0002-1383-8246
2015 (engelsk)Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 80, nr 22, s. 11529-11537Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

N-heterocyclic carbene-phosphine iridium complexes (NHC-Ir) were developed/found to be a highly reactive catalyst for N-monoalkylation of amides with alcohols via hydrogen transfer. The reaction produced the desired product in high isolated yields using a wide range of substrates with low catalyst loading and short reaction times.

sted, utgiver, år, opplag, sider
2015. Vol. 80, nr 22, s. 11529-11537
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-119680DOI: 10.1021/acs.joc.5b01324ISI: 000365462600033OAI: oai:DiVA.org:su-119680DiVA, id: diva2:847684
Forskningsfinansiär
Swedish Research CouncilStiftelsen Olle Engkvist ByggmästareSwedish Energy AgencyKnut and Alice Wallenberg FoundationBerzelii Centre EXSELENTTilgjengelig fra: 2015-08-21 Laget: 2015-08-21 Sist oppdatert: 2019-12-04bibliografisk kontrollert
Inngår i avhandling
1. Hydrogenation, Transfer Hydrogenation and Hydrogen Transfer Reactions Catalyzed by Iridium Complexes
Åpne denne publikasjonen i ny fane eller vindu >>Hydrogenation, Transfer Hydrogenation and Hydrogen Transfer Reactions Catalyzed by Iridium Complexes
2015 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The work described in this thesis is focused on the development of new bidentate iridium complexes and their applications in the asymmetric reduction of olefins, ketones and imines. Three new types of iridium complexes were synthesized, which included pyridine derived chiral N,P-iridium complexes, achiral NHC complexes and chiral NHC-phosphine complexes. A study of their catalytic applications demonstrated a high efficiency of the N,P-iridium complexes for asymmetric hydrogenation of olefins, with good enantioselectivity. The carbene complexes were found to be very efficient hydrogen transfer mediators capable of abstracting hydrogen from alcohols and subsequently transfer it to other unsaturated bonds. This hydrogen transferring property of the carbene complexes was used in the development of C–C and C–N bond formation reactions via the hydrogen borrowing process. The complexes displayed high catalytic reactivity using 0.5–1.0 mol% of the catalyst and mild reaction conditions. Finally chiral carbene complexes were found to be activated by hydrogen gas. Their corresponding iridium hydride species were able to reduce ketones and imines with high efficiency and enantioselectivity without any additives, base or acid.

sted, utgiver, år, opplag, sider
Stockholm: Department of Organic Chemistry, Stockholm University, 2015. s. 69
Emneord
Iridium catalyst, carbene, N, P - ligand, asymmetric hydrogenation, transfer hydrogenation, hydrogen transfer reaction, alkylation, olefin, ketone, amide
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-119701 (URN)978-91-7649-255-0 (ISBN)
Disputas
2015-09-30, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:15 (engelsk)
Opponent
Veileder
Merknad

At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 5: Submitted. Paper 6: Manuscript.

 

Tilgjengelig fra: 2015-09-08 Laget: 2015-08-21 Sist oppdatert: 2015-09-08bibliografisk kontrollert
2. 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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