Catalytic Iodination of the Aliphatic C-F Bond by YbI3(THF)(3): Mechanistic Insight and Synthetic Utility
Journal article, 2016
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).
fluorination
Chemistry
alkyl fluorides
iodotrimethylsilane
chemistry
substitution
conversion
activation
hydrodefluorination
reagents
alcohols
Author
Mario Janjetovic
University of Gothenburg
Andreas Ekebergh
University of Gothenburg
Annika M. Träff
University of Gothenburg
Göran Hilmersson
University of Gothenburg
Organic Letters
1523-7060 (ISSN) 1523-7052 (eISSN)
Vol. 18 12 2804-2807Subject Categories
Biological Sciences
Chemical Sciences
DOI
10.1021/acs.orglett.6b01022