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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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Article information


Submitted
14 May 2018
Accepted
28 Jun 2018
First published
28 Jun 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 6411-6416
Article type
Edge Article

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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