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Microwave-Assisted Asymmetric Intermolecular Heck Reaction using Phosphine-Thiazole Ligands
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
2007 (engelsk)Inngår i: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, nr 7-18, s. 2595-2602Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

A series of new phosphine-thiazole compounds has been synthesized and used as efficient ligands in the palladium-catalyzed asymmetric intermolecular Heck coupling of 2,3-dihydrofuran with aryl triflates and cyclohexenyl triflate. Microwave heating was used to accelerate the reactions and gave complete conversions in as little as one hour. Products were obtained with good to excellent enantioselectivities.

sted, utgiver, år, opplag, sider
2007. Vol. 349, nr 7-18, s. 2595-2602
Emneord [en]
asymmetric catalysis, Heck reaction, microwave heating, phosphine-thiazole ligands
HSV kategori
Identifikatorer
URN: urn:nbn:se:uu:diva-12345DOI: 10.1002/adsc.200700390OAI: oai:DiVA.org:uu-12345DiVA, id: diva2:40114
Tilgjengelig fra: 2007-12-13 Laget: 2007-12-13 Sist oppdatert: 2017-12-11bibliografisk kontrollert
Inngår i avhandling
1. Synthesis and Evaluation of N,P-Chelating Ligands in Asymmetric Transition-Metal-Catalyzed Reactions: Ir-Catalyzed Asymmetric Hydrogenation and Pd-Catalyzed Asymmetric Intermolecular Heck Reaction
Åpne denne publikasjonen i ny fane eller vindu >>Synthesis and Evaluation of N,P-Chelating Ligands in Asymmetric Transition-Metal-Catalyzed Reactions: Ir-Catalyzed Asymmetric Hydrogenation and Pd-Catalyzed Asymmetric Intermolecular Heck Reaction
2009 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

This thesis describes synthesis of new chiral N,P ligands and their evaluation in two types of asymmetric transition-metal catalyzed reactions.

The first part of the thesis describes studies in iridium-catalyzed asymmetric hydrogenation. A new class of chiral N,P ligands, imidazole-phosphines, was synthesized and evaluated in the Ir-catalyzed asymmetric hydrogenation of olefins (Paper I). The new ligands proved to be highly efficient and enantioselective in the reaction. Because the substrate scope of Ir-catalyzed asymmetric hydrogenation is still limited to certain types of test substrates, new substrate classes with importance in medicinal and materials chemistry were investigated. Vinyl fluorides were efficiently hydrogenated to fluorine-containing chiral centers by the iridium catalysts with imidazole-phosphine ligands (Paper I). To obtain CF3-bearing chiral centers, we hydrogenated CF3-substituted olefins (Paper II). Ir-catalyzed asymmetric  hydrogenation was highly enantioselective for the functionalized CF3-substituted olefins and the resulting chiral products can be valuable in design of materials such as LCD screens. Ir-catalyzed asymmetric hydrogenation was also evaluated as a route to diarylmethine chiral centers (Paper III). A wide range of new chiral compounds possessing a diarylmethine chiral center was obtained.

The second part of the thesis deals with asymmetric intermolecular Heck reaction utilizing N,P ligands. The N,P ligand class of thiazole-phosphines was evaluated in the Heck reaction (Paper IV) and gave high enantioselectivity. Further, the intermolecular Heck reaction was examined using computational and experimental studies (Paper V). This study led to a better understanding of the enantioselectivity in the reaction.

sted, utgiver, år, opplag, sider
Uppsala: Acta Universitatis Upsaliensis, 2009. s. 74
Serie
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 681
Emneord
Asymmetric hydrogenation, Heck reaction, N, P ligand, Iridium, Palladium, Asymmetric catalysis, Alkenes, Fluorine, Diarylmethine stereocenters
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
urn:nbn:se:uu:diva-108940 (URN)978-91-554-7632-8 (ISBN)
Disputas
2009-11-26, sal B41, BMC, Husargatan 3, Uppsala, 10:15 (engelsk)
Opponent
Veileder
Tilgjengelig fra: 2009-11-05 Laget: 2009-10-05 Sist oppdatert: 2009-11-05bibliografisk kontrollert

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