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Microwave-promoted palladium(II)-catalyzed C-P bond formation by using arylboronic acids or aryltrifluoroborates.
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. ORGFARM.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical and Analytical Chemistry.
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2009 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 47, 13069-13074 p.Article in journal (Refereed) Published
Abstract [en]

The first Pd-II-catalyzed P arylation has been performed by using palladium acetate, the rigid bidentate ligand dmphen (dmphen=2,9-dimethyl-1,10-phenanthroline), and without the addition of base or acid. Couplings of arylboronic acids or aryl trifluoroborates with H-phosphonate dialkyl esters were conducted in 30 min with controlled microwave (MW) heating under non-inert conditions. Aryl phosphites were also synthesized at room temperature with atmospheric air as the sole reoxidant. The arylated phosphonates were isolated in 44-90% yields. The excellent chemoselectivity of the method was illustrated in the synthesis of a Mycobacterium tuberculosis glutamine synthetase (MTB-GS) inhibitor. Online ESIMS was used to detect cationic palladium species in ongoing reactions directly, and a catalytic cycle has been proposed based on these results.

Place, publisher, year, edition, pages
Weinheim: Wiley-VCH Verlag GmbH , 2009. Vol. 15, no 47, 13069-13074 p.
Keyword [en]
Boronic acids, microwave chemistry, palladium, P arylation, trifluoroborates
National Category
Analytical Chemistry
Research subject
Analytical Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-113919DOI: 10.1002/chem.200901473ISI: 000273697100021PubMedID: 19856344OAI: oai:DiVA.org:uu-113919DiVA: diva2:292144
Available from: 2010-02-04 Created: 2010-02-04 Last updated: 2017-12-12Bibliographically approved

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Lindh, JonasSävmarker, JonasSjöberg, Per J.R.Larhed, Mats

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Organic Pharmaceutical ChemistryDepartment of Medicinal ChemistryDepartment of Physical and Analytical Chemistry
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Analytical Chemistry

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