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Fluorinated cyclopropanes: Synthesis and chemistry of the aryl α,β,β-trifluorocyclopropane motif

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Author(s)

Connor Thomson, Qingzhi Zhang, Nawaf Al-Maharik, Michael Buehl, David Bradford Cordes, Alexandra Slawin, David O'Hagan

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Abstract

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.
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Original languageEnglish
JournalChemical Communications
VolumeIn press
Early online date3 Jul 2018
DOIs
Publication statusE-pub ahead of print - 3 Jul 2018

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