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Catalytic Iodination of the Aliphatic C-F Bond by YbI3(THF)(3): Mechanistic Insight and Synthetic Utility

Journal article
Authors Mario Janjetovic
Andreas Ekebergh
Annika M. Träff
Göran Hilmersson
Published in Organic Letters
Volume 18
Issue 12
Pages 2804-2807
ISSN 1523-7060
Publication year 2016
Published at Department of Chemistry and Molecular Biology
Pages 2804-2807
Language en
Links dx.doi.org/10.1021/acs.orglett.6b01...
Keywords alkyl fluorides, activation, fluorination, hydrodefluorination, substitution, chemistry, iodotrimethylsilane, conversion, reagents, alcohols, Chemistry
Subject categories Chemical Sciences, Biological Sciences

Abstract

A facile iodination protocol, of unactivated alkyl fluorides: using catalytic amounts of YbI3(THF)(3) in the presence of iodotrimethylsilane as a stoichiometric fluoride trapping agent is presented. H-1 NMR spectroscopy demonstrates a two-step :catalytic cycle where TMSI regenerates active YbI3(THF)(3). Finally, the catalytic reaction is extended a one-pot procdure to demonstrate a potential application of the method Overall, the findings present a distinct strategy for C-F bond transformations in the presence of catalytic YbI3(THF)(3).

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