A facile route to polysubstituted 2-pyrones from readily available 2-acylcyclopropane-1-aryl-1-carboxylates mediated by TfOH is reported. The strongly donating 1-aryl group is important for directing the C-C bond cleavage of the donor-acceptor cyclopropane ring, which then leads to the formation of the 2-pyrone ring through lactonization.
Formal homo-Nazarov cyclization of benzonorcaradienes produced by intramolecular hydroarylation of arylated alkynylcyclopropanes promoted by TfOH has been described, providing stereoselective access to highly substituted hydrochrysenes. An unprecedented 1,2-acyl migration occurred for the 2-heteroaroyl substrates, thus giving the same products as their 3heteroaroyl analogs. Moreover, these products could be readily oxidized by air to fully π-conjugated chrysenes after decarboxylation.
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