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Issue 30, 2018
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Ring-opening hydroarylation of monosubstituted cyclopropanes enabled by hexafluoroisopropanol

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Abstract

Ring-opening hydroarylation of cyclopropanes is typically limited to substrates bearing a donor–acceptor motif. Here, the transformation is achieved for monosubstituted cyclopropanes by using catalytic Brønsted acid in hexafluoroisopropanol (HFIP) solvent, constituting a rare example where such cyclopropanes engage in intermolecular C–C bond formation. Branched products are obtained when electron-rich arylcyclopropanes react with a broad scope of arene nucleophiles in accord with a simple SN1-type ring-opening mechanism. In contrast, linear products are obtained when cyclopropylketones react with electron-rich arene nucleophiles. In the latter case, mechanistic experiments and DFT-calculations support a homo-conjugate addition pathway.

Graphical abstract: Ring-opening hydroarylation of monosubstituted cyclopropanes enabled by hexafluoroisopropanol

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Publication details

The article was received on 14 May 2018, accepted on 28 Jun 2018 and first published on 28 Jun 2018


Article type: Edge Article
DOI: 10.1039/C8SC02126K
Citation: Chem. Sci., 2018,9, 6411-6416
  • Open access: Creative Commons BY-NC license
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    Ring-opening hydroarylation of monosubstituted cyclopropanes enabled by hexafluoroisopropanol

    E. Richmond, J. Yi, V. D. Vuković, F. Sajadi, C. N. Rowley and J. Moran, Chem. Sci., 2018, 9, 6411
    DOI: 10.1039/C8SC02126K

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