Ring-Opening Hydroarylation of Monosubstituted Cyclopropanes Enabled by Hexafluoroisopropanol

16 May 2018, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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 constrast, 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.

Keywords

cyclopropanes
HFIP
hydroarylation
Friedel-Crafts
homo-conjugate addition

Supplementary materials

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