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 2804-2807

Subject Categories

Biological Sciences

Chemical Sciences

DOI

10.1021/acs.orglett.6b01022

More information

Created

10/10/2017