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C-11-Carbonylation through in Situ Generated C-11-Benzoyl Chlorides with Tetrabutylammonium Chloride as Chloride Source
Karolinska Insititute, Ctr Psychiat Res, Karolinska Hosp, Dept Clin Neurosci, SE-17176 Stockholm, Sweden..
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
2017 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 18, 2648-2651 p.Article in journal (Refereed) Published
Abstract [en]

Aromatic C-11-containing acids, amides, esters, and aldehydes were obtained through a novel C-11-carbonylative reaction. In the two-step process, aryl iodides are first reacted with (CO)-C-11 and tetrabutylammonium chloride in a palladium-mediated reaction to yield C-11-benzoyl chlorides in situ. The crude mixture is then further treated with either a hydroxide, amine, alcohol, or a hydride in a second vial to furnish the final C-11-carbonyl product. The monodentate ligand tri-tert-butylphosphonium tetrafluoroborate was proven to be crucial for obtaining high radiochemical yields (RCY). A wide range of C-11-containing carbonyl compounds were successfully radiolabeled in moderate to excellent RCYs, ranging from 41-93%. The synthetic retinoic acid tamibarotene was obtained in a RCY of 89%, whereas the Boc-protected procainamide was labelled in 68% RCY, which is a significantly increase (2-3 fold) in RCY compared to other published methods.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2017. no 18, 2648-2651 p.
Keyword [en]
Isotopes, Carbonylation, Positron emission tomography, Benzoyl chlorides, Palladium
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-325330DOI: 10.1002/ejoc.201700268ISI: 000401434900015OAI: oai:DiVA.org:uu-325330DiVA: diva2:1119217
Available from: 2017-07-03 Created: 2017-07-03 Last updated: 2017-07-03Bibliographically approved

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CiteExportLink to record
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