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Janjetovic M, Ekebergh A, Träff AM, et al. Catalytic Iodination of the Aliphatic C-F Bond by YbI3(THF)3: Mechanistic Insight and Synthetic Utility. Org Lett. 2016;18(12):2804-7doi: 10.1021/acs.orglett.6b01022.
Janjetovic, M., Ekebergh, A., Träff, A. M., & Hilmersson, G. (2016). Catalytic Iodination of the Aliphatic C-F Bond by YbI3(THF)3: Mechanistic Insight and Synthetic Utility. Organic letters, 18(12), 2804-7. https://doi.org/10.1021/acs.orglett.6b01022
Janjetovic, Mario, et al. "Catalytic Iodination of the Aliphatic C-F Bond by YbI3(THF)3: Mechanistic Insight and Synthetic Utility." Organic letters vol. 18,12 (2016): 2804-7. doi: https://doi.org/10.1021/acs.orglett.6b01022
Janjetovic M, Ekebergh A, Träff AM, Hilmersson G. Catalytic Iodination of the Aliphatic C-F Bond by YbI3(THF)3: Mechanistic Insight and Synthetic Utility. Org Lett. 2016 Jun 17;18(12):2804-7. doi: 10.1021/acs.orglett.6b01022. Epub 2016 May 31. PMID: 27243465.
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Org Lett. 2016 Jun 17;18(12):2804-7. doi: 10.1021/acs.orglett.6b01022. Epub 2016 May 31.

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

Organic letters

Mario Janjetovic, Andreas Ekebergh, Annika M Träff, Göran Hilmersson

Affiliations

  1. Department of Chemistry and Molecular Biology, University of Gothenburg , Kemivägen 10, SE-412 96 Gothenburg, Sweden.

PMID: 27243465 DOI: 10.1021/acs.orglett.6b01022

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. (1)H NMR spectroscopy demonstrates a two-step catalytic cycle where TMSI regenerates active YbI3(THF)3. Finally, the catalytic reaction is extended into a one-pot procedure 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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