Ring-opening hydroarylation of monosubstituted cyclopropanes enabled by hexafluoroisopropanol?

Chemical Science Pub Date: 2018-06-28 DOI: 10.1039/C8SC02126K

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 Br?nsted 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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