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Diarylated Ethanones from Mo(CO)(6)-Mediated and Microwave-Assisted Palladium-Catalysed Carbonylative Negishi Cross-Couplings
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.
2013 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2013, no 22, 4729-4733 p.Article in journal (Refereed) Published
Abstract [en]

Two protocols for palladium-catalysed carbonylative Negishi cross-couplings were developed for aryl iodides and aryl bromides. The two main breakthroughs were that molybdenum hexacarbonyl [Mo(CO)(6)] could be used as a solid in situ source of CO, and that controlled microwave irraditaion could be used for heating. Consequently, the reactions were safe (in contrast to when CO gas was used) and fast (in comparison to when conventional heating was used). The carbonylative cross-coupling reactions were carried out using commercially available benzylzinc bromide in closed vials (90-120 degrees C for 0.5-1 h) to give a set of diarylated ethanones, a common pharmacophore found in several pharmaceuticals, in moderate to high isolated yields (47-84%). The mild three-component carbonylation protocol presented here is operationally simple, safe, and rapid, and the formation of the carbonylative Negishi cross-coupling product is favoured over the product of Negishi cross-coupling.

Place, publisher, year, edition, pages
2013. Vol. 2013, no 22, 4729-4733 p.
Keyword [en]
Carbonylation, Cross-coupling, Palladium, Homogeneous catalysis, Metal carbonyls, Microwave chemistry
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-220939DOI: 10.1002/ejoc.201300610ISI: 000331293500002OAI: oai:DiVA.org:uu-220939DiVA: diva2:707343
Available from: 2014-03-24 Created: 2014-03-24 Last updated: 2017-12-05Bibliographically approved

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Motwani, Hitesh V.Larhed, Mats

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