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The Use of Lithium Amides in the Palladium-Mediated Synthesis of [Carbonyl-11C]Amides
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry. (Bengt Långström)
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
2007 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2007, no 26, 4337-4342 p.Article in journal (Refereed) Published
Abstract [en]

Weakly nucleophilic amines were converted into the corresponding lithium amides and used in either one- or two-pot palladium mediated-reactions with [11C]carbon monoxide and aryl iodides. It was found that palladium acyl complexes may be prepared in a separate step and have sufficient lifetime to be used in a subsequent reaction with a nucleophile. This two-pot procedure was used for the labelling synthesis of eleven amides (nine of which are analogues of WAY-100635, a 5-HT1A radioligand) from weakly nucleophilic amines. The results were compared to a direct one-pot procedure using lithium amides. Both approaches extend the scope of palladium-mediated carbonylation using [11C]carbon monoxide and aryl iodides allowing use of weakly nucleophilic amines.

Place, publisher, year, edition, pages
Weinheim, Germany: Wiley , 2007. Vol. 2007, no 26, 4337-4342 p.
Keyword [en]
Carbon monoxide, carbonylation, palladium, lithium, amides
National Category
Other Basic Medicine
Identifiers
URN: urn:nbn:se:uu:diva-106710DOI: 10.1002/ejoc.200700255ISI: 000249797200009OAI: oai:DiVA.org:uu-106710DiVA: diva2:236742
Available from: 2009-09-24 Created: 2009-06-29 Last updated: 2017-12-13Bibliographically approved

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