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C–F bond activation of perfluorinated arenes by a bioxazoline-derived N-heterocyclic carbene

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Emerson-King, Jack, Hauser, Simone A. and Chaplin, Adrian B. (2017) C–F bond activation of perfluorinated arenes by a bioxazoline-derived N-heterocyclic carbene. Organic and Biomolecular Chemistry, 15 (4). pp. 787-789. doi:10.1039/C6OB02556K

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Official URL: http://dx.doi.org/10.1039/C6OB02556K

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Abstract

The N-heterocyclic carbene IBioxMe4 enacts selective single and double C–F bond activation of octafluorotoluene and hexafluorobenzene, respectively. The formation of the fluoroarene substituted, zwitterionic imidazoliumolate products is consistent with a mechanism involving nucleophilic aromatic substitution and subsequent oxazoline ring opening by liberated fluoride.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH): Carbenes (Methylene compounds), Aromatic compounds, Organic compounds -- Synthesis, Heterocyclic compounds
Journal or Publication Title: Organic and Biomolecular Chemistry
Publisher: RSC
ISSN: 1477-0520
Official Date: 22 December 2017
Dates:
DateEvent
22 December 2017Published
13 December 2016Accepted
22 November 2016Submitted
Date of first compliant deposit: 2 March 2017
Volume: 15
Number: 4
Page Range: pp. 787-789
DOI: 10.1039/C6OB02556K
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Open Access
Funder: Engineering and Physical Sciences Research Council (EPSRC), Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung [Swiss National Science Foundation] (SNSF), Royal Society (Great Britain), University of Warwick, Advantage West Midlands (AWM), European Regional Development Fund (ERDF)

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