Fluorinated cyclopropanes : Synthesis and chemistry of the aryl α,β,β-trifluorocyclopropane motif
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A general route to aryl α,β,β-trifluorocyclopropanes is reported and aryl oxidation gave the corresponding α,β,β-trifluorocyclopropane carboxylic acid. Reactions of the corresponding amides with phenol/thiophenol resulted in HF elimination and then conjugate addition. The partially fluorinated cyclopropane has a similar lipophilicity to –CF3 despite three carbon atoms, and it emerges as a novel motif for drug discovery.
Thomson , C , Zhang , Q , Al-Maharik , N , Buehl , M , Cordes , D B , Slawin , A & O'Hagan , D 2018 , ' Fluorinated cyclopropanes : Synthesis and chemistry of the aryl α,β,β-trifluorocyclopropane motif ' , Chemical Communications , vol. In press . https://doi.org/10.1039/C8CC04964E
© 2018 the Authors. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1039/C8CC04964E
DescriptionThe authors are grateful to the EPSRC for supporting this work. The authors acknowledge the EPSRC National Mass Spectrometry Facility (Swansea) and D.O’H. thanks the Royal Society for a Wolfson Research Merit Award.
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