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Alkyl Iodides and [C-11]CO in Nickel-Mediated Cross-Coupling Reactions: Successful Use of Alkyl Electrophiles containing a beta Hydrogen Atom in Metal-Mediated [C-11]Carbonylation
Karolinska Univ Hosp, Karolinska Inst, Ctr Psychiat Res, Dept Clin Neurosci, S-17176 Stockholm, Sweden.;Bencar AB, Dag Hammarsjoldsvag 34B, S-57237 Uppsala, Sweden..
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry. Bencar AB, Dag Hammarsjoldsvag 34B, S-57237 Uppsala, Sweden.
Karolinska Univ Hosp, Karolinska Inst, Ctr Psychiat Res, Dept Clin Neurosci, S-17176 Stockholm, Sweden..
2016 (English)In: CHEMISTRYSELECT, ISSN 2365-6549, Vol. 1, no 10, 2498-2501 p.Article in journal (Refereed) Published
Abstract [en]

Transition metal-mediated cross-coupling reactions of non-activated alkyl electrophiles suffer from competing b-hydride elimination and therefore have limited applications in synthetic organic chemistry. Hereby the first successful use of nickel-mediated carbonylative cross-coupling of non-activated alkyl iodides using [C-11] carbon monoxide is presented. The reaction conditions were optimised for the synthesis of N-(pyridine-2-yl) cyclohexane([C-11] carbonyl)-carboxamide. The nickel(0) complex, Ni(COD) 2, in the presence of bathophenanthroline in the non-polar protic solvent tert-butanol at 100 degrees C offered the highest trapping efficiency (TE) and radiochemical yield (RCY) of 89% and 72%, respectively. The applicability of the method was further explored in the syntheses of five additional ([C-11] carbonyl) amides (6a to 6e in Figure 2) and the TE and RCY in the latter cases were 70-90% and 33-57%, respectively. The presented method has a potential for the development of C-11-labelled PET tracers with a carbonyl group connected to an alkyl chain containing beta hydrogen.

Place, publisher, year, edition, pages
2016. Vol. 1, no 10, 2498-2501 p.
Keyword [en]
[C-11]carbonylation, PET, alkyl iodides, nickel-mediated, cross-coupling
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-319900DOI: 10.1002/slct.201600643ISI: 000395417800063OAI: oai:DiVA.org:uu-319900DiVA: diva2:1087955
Available from: 2017-04-10 Created: 2017-04-10 Last updated: 2017-04-10Bibliographically approved

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