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

The 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.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.PostprintPostprintPeer reviewe