Fluorinated cyclopropanes : Synthesis and chemistry of the aryl α,β,β-trifluorocyclopropane motif
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.
Citation
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
Publication
Chemical Communications
Status
Peer reviewed
ISSN
1359-7345Type
Journal article
Description
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.Collections
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