Abstract
The cycloaromatization of aromatic aldehydes and ketones was readily achieved by using a Brønsted acid catalyst in 1,1,1,3,3,3‐hexafluoropropan‐2‐ol (HFIP). In the presence of a catalytic amount of trifluoromethanesulfonic acid, biaryl‐2‐ylacetaldehydes and 2‐benzylbenzaldehydes underwent sequential intramolecular cationic cyclization and dehydration to afford phenacenes and acenes, respectively. Furthermore, biaryl‐2‐ylacetaldehydes bearing a cyclopentene moiety at the α‐position underwent unprecedented cycloaromatization including ring expansion to afford triphenylenes. HFIP effectively promoted the cyclizations by suppressing side reactions presumably as a result of stabilization of the cationic intermediates.
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