77549-02-1Relevant academic research and scientific papers
Ring-opening hydroarylation of monosubstituted cyclopropanes enabled by hexafluoroisopropanol
Richmond, Edward,Yi, Jing,Vukovi?, Vuk D.,Sajadi, Fatima,Rowley, Christopher N.,Moran, Joseph
, p. 6411 - 6416 (2018)
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.
