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Metathesis Mechanism of Zinc-Catalyzed Fluorination of Alkenes with Hypervalent Fluoroiodine
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 3
2017 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 7, no 2, 1093-1100 p.Article in journal (Refereed) Published
Abstract [en]

Density functional theory calculations are used to unravel the mechanism of the Zn-catalyzed fluorocyclization reaction of alkenes using fluoro-benziodoxole reagent. In the initial step Zn coordinates to the fluorine atom of the fluoro-benziodoxole reagent. An important activation step for the fluorination involves Zn-mediated isomerization of the benziodoxole reagent. The activation is followed by a metathesis step to form the C-F bond and a nucleophilic substitution, closing the ring to yield the final aminofluorination product. This mechanism has feasible energy barriers and accounts for the observed selectivity outcome. An alternative mechanism involving an iodocyclopropylium cation intermediate is shown to be associated with high energies.

Place, publisher, year, edition, pages
2017. Vol. 7, no 2, 1093-1100 p.
Keyword [en]
fluorination, hypervalent iodine, mechanism, catalysis, metathesis, density functional theory
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-141370DOI: 10.1021/acscatal.6b02731ISI: 000393539200019OAI: oai:DiVA.org:su-141370DiVA: diva2:1091999
Available from: 2017-04-28 Created: 2017-04-28 Last updated: 2017-04-28Bibliographically approved

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Szabó, Kálmán J.Himo, Fahmi
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