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Open-air oxidative Heck reactions at room temperature
Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för organisk farmaceutisk kemi.
2006 (engelsk)Inngår i: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270, Vol. 8, nr 4, s. 338-343Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Palladium(II)-catalyzed oxidative Heck arylation reactions proceed at room temperature with atmospheric air as the sole reoxidant. Using arylboronic acids as arylating agents and inexpensive 2,9-dimethyl-1,10-phenanthroline as the supporting ligand, efficient vinylic substitution reactions were obtained both with electron-poor and electron-rich olefins on a 1–50 mmol scale.

sted, utgiver, år, opplag, sider
2006. Vol. 8, nr 4, s. 338-343
HSV kategori
Identifikatorer
URN: urn:nbn:se:uu:diva-94792DOI: 10.1039/B517152KOAI: oai:DiVA.org:uu-94792DiVA, id: diva2:168775
Tilgjengelig fra: 2006-09-14 Laget: 2006-09-14 Sist oppdatert: 2017-12-14bibliografisk kontrollert
Inngår i avhandling
1. Novel Metal-Mediated Organic Transformations: Focusing on Microwave Acceleration and the Oxidative Heck Reaction
Åpne denne publikasjonen i ny fane eller vindu >>Novel Metal-Mediated Organic Transformations: Focusing on Microwave Acceleration and the Oxidative Heck Reaction
2006 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

Transition metals have played an important role in synthetic organic chemistry for more than a century, and offer catalytic transformations that would have been impossible with classical chemistry. One of the most useful and versatile of the transition metals is palladium, which over the years has catalyzed many important carbon-carbon forming reactions. Popular cross-coupling reactions such as the Suzuki, Stille and the Heck reaction are all catalyzed by palladium, or more correctly, by palladium in its ground state, Pd(0).

Recently, interest in palladium(II)-catalyzed transformations has started to grow, partly due to the development of the vinylic substitution reaction, commonly called the oxidative Heck reaction, presented in this thesis. This Pd(II)-catalyzed, ligand-modulated reaction occurs under air at room temperature, and for the first time a general protocol employing a wide range of olefins and arylboronic acids was obtained. Ligand screening showed that the bidentate nitrogen ligand, 2,9-dimethyl-1,10-phenanthroline (dmphen), was the most suitable ligand. Dmphen is believed to facilitate regeneration of active Pd(II), increase catalytic stability and improve the regioselectivity in the reaction. A mechanistic investigation was conducted using electrospray ionization mass spectrometry (ESI-MS), making it possible to observe cationic intermediates in a productive oxidative Heck arylation. The results obtained are in agreement with the previously proposed catalytic cycle.

The emerging discipline of high-speed synthesis is making contributions to society’s growing demand for new chemical entities. This inspired the development of two ultrafast, microwave-accelerated carbonylation reactions with dicobalt octacarbonyl acting both as an in situ carbon monoxide supplier and reaction mediator. A wide range of symmetrical benzophenones was produced in only 6 to 10 s, using aryl iodides as the substrate. The second carbonylation reaction provided symmetrical and unsymmetrical ureas in process times ranging from 10 s to 40 minutes using primary and secondary amines.

sted, utgiver, år, opplag, sider
Uppsala: Acta Universitatis Upsaliensis, 2006. s. 77
Serie
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Pharmacy, ISSN 1651-6192 ; 37
Emneord
Organic chemistry, palladium(II), oxidative Heck reaction, high-throughput-chemistry, microwave acceleration, dicobalt octacarbonyl, in situ carbonylation, urea, diaryl ketones, ESI-MS, Organisk kemi
Identifikatorer
urn:nbn:se:uu:diva-7117 (URN)91-554-6638-9 (ISBN)
Disputas
2006-10-06, B41, BMC, Husargatan 3, Uppsala, 09:15
Opponent
Veileder
Tilgjengelig fra: 2006-09-14 Laget: 2006-09-14bibliografisk kontrollert

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