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

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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.

Graphical abstract: Fluorinated cyclopropanes: synthesis and chemistry of the aryl α,β,β-trifluorocyclopropane motif

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Publication details

The article was received on 21 Jun 2018, accepted on 03 Jul 2018 and first published on 03 Jul 2018


Article type: Communication
DOI: 10.1039/C8CC04964E
Citation: Chem. Commun., 2018, Advance Article
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    Fluorinated cyclopropanes: synthesis and chemistry of the aryl α,β,β-trifluorocyclopropane motif

    C. J. Thomson, Q. Zhang, N. Al-Maharik, M. Bühl, D. B. Cordes, A. M. Z. Slawin and D. O’Hagan, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC04964E

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