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Efficient palladium(II) catalysis under air. Base-free oxidative heck reactions at room temperature or with microwave heating
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. (ORGFARM)
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. (ORGFARM)
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. (ORGFARM)
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2007 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 72, no 21, 7957-7962 p.Article in journal (Refereed) Published
Abstract [en]

Scope and limitations of the base-free oxidative Heck reaction with arylboronic acids have been explored. Under our conditions, the dmphen−palladium(II)-catalyzed arylation proceeded with air or p-benzoquinone as reoxidants of palladium(0). We found that ambient temperature and mild aerobic conditions allow for the use of substrates sensitive to palladium(II)-catalyzed oxidation. Oxidative Heck couplings, employing different arylboronic acids, were smoothly and regioselectively conducted with both electron-rich and electron-poor olefins, providing high yields even with disubstituted butyl methacrylate, sensitive acrolein, and a vinylboronate ester. Controlled microwave processing was used to reduce reaction times from hours to minutes both in small scale and in 50 mmol scale batch processes.

Place, publisher, year, edition, pages
2007. Vol. 72, no 21, 7957-7962 p.
Keyword [en]
Acrylates/*chemistry, Aerobiosis, Benzene Derivatives/*chemistry, Boronic Acids/*chemistry, Catalysis, Chemistry; Organic/*methods, Heat, Microwaves, Oxidation-Reduction, Palladium/*chemistry, Temperature
National Category
Pharmaceutical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-16615DOI: 10.1021/jo701434sISI: 000249986500019PubMedID: 17887706OAI: oai:DiVA.org:uu-16615DiVA: diva2:44386
Available from: 2008-05-29 Created: 2008-05-29 Last updated: 2017-12-08Bibliographically approved

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Lindh, JonasLarhed, Mats

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