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Arylboronic acids as versatile coupling partners in fast microwave promoted oxidative Heck chemistry
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
2003 (English)In: Molecular diversity, ISSN 1381-1991, E-ISSN 1573-501X, Vol. 7, no 2-4, 97-106 p.Article in journal (Refereed) Published
Abstract [en]

The useful and selective reactivity of arylboronic acids makes them favourite building blocks for many modern organic chemistry applications like the metal-mediated formation of C-C, C-O, C-N, and C-S bonds. This report describes oxidative Heck coupling reactions of arylboronic acids and olefins, which were conveniently and rapidly (5-30 min) carried out under air with temperature-controlled microwave heating. Different reaction conditions were investigated with regard to both microwave heating capability and chemical productivity. Copper(II) acetate was identified as a microwave compatible reoxidant of Pd(0). The scope and limitations of this high-speed chemistry protocol with diverse olefins and organoboronic acids are discussed.

Place, publisher, year, edition, pages
2003. Vol. 7, no 2-4, 97-106 p.
National Category
Medical and Health Sciences
Identifiers
URN: urn:nbn:se:uu:diva-90947DOI: 10.1023/B:MODI.0000006803.99656.8cPubMedID: 14870838OAI: oai:DiVA.org:uu-90947DiVA: diva2:163477
Available from: 2003-10-27 Created: 2003-10-27 Last updated: 2017-12-14Bibliographically approved
In thesis
1. Selectivity in Palladium- and Enzyme-Catalyzed Reactions: Focusing on Enhancement of Reactivity
Open this publication in new window or tab >>Selectivity in Palladium- and Enzyme-Catalyzed Reactions: Focusing on Enhancement of Reactivity
2003 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Catalysis has a profound impact on all living species on the earth. Nature’s catalysts, the enzymes, have the ability to selectively promote a specific bio-chemical transformation, given the required substrate. As well as being highly selective, enzymes enhance the speed of these reactions, helping them to run at temperatures much lower than normally required, i.e. at body temperature. In comparison, reactions used in the production of new materials such as polymers, medicines, fragrances, petrochemicals, etc. are often catalyzed by transition metals. This thesis describes how the selectivity and activity of these catalysts can be influenced via two conceptually different methods: chelation control and microwave heating. The thesis primarily focuses on regio- and stereochemical aspects of the palladium-catalyzed arylation of olefins, i.e. the Heck reaction. Reaction rate enhancement of both palladium and enzyme (polymerase chain reaction [PCR]) catalysis by microwave heating is also discussed.

Novel chelation-controlled palladium-catalyzed multi- and asymmetric arylations of vinyl ethers were performed, resulting in tetra-substituted olefins as well as chiral quaternary carbon centers with excellent optical purity. In addition, a new synthetic route to diarylated ethanals, relying on a double chelation-controlled regioselective arylation followed by hydrolysis, has been discovered. High temperature conditions, using microwave heating, substantially reduce the reaction time for ligand-controlled asymmetric Heck arylations, while retaining levels of enantioselectivity in most cases. In addition, a potentially useful fast synthetic protocol for the employment of aryl boronic acids in oxidative Heck arylation was developed. Finally, microwave-assisted PCR was described for the first time; this method allows reductions in the run time of 50%.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2003. 76 p.
Series
Comprehensive Summaries of Uppsala Dissertations from the Faculty of Pharmacy, ISSN 0282-7484 ; 299
Keyword
Pharmaceutical chemistry, Palladium, Heck, PCR, Microwaves, Farmaceutisk kemi
National Category
Medicinal Chemistry
Identifiers
urn:nbn:se:uu:diva-3625 (URN)91-554-5765-7 (ISBN)
Public defence
2003-11-21, B41, BMC, Uppsala, 13:15
Opponent
Supervisors
Available from: 2003-10-27 Created: 2003-10-27Bibliographically approved

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Larhed, Mats

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