Issue 30, 2018

Ring-opening hydroarylation of monosubstituted cyclopropanes enabled by hexafluoroisopropanol

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

Supplementary files

Article information

Article type
Edge Article
Submitted
14 mei 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
Creative Commons BY-NC license

Chem. Sci., 2018,9, 6411-6416

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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