jo990454i_si_001.pdf (331.97 kB)
Synthesis of Aryl-Substituted Piperidines by Superacid Activation of Piperidones
journal contribution
posted on 1999-08-13, 00:00 authored by Douglas A. Klumpp, Manuel Garza, Andre Jones, Saray MendozaDiarylpiperidines (8−12) may be prepared in good to excellent yields (80−99%) by the reaction of
piperidones (3d−h) with benzene and the Bronsted superacid, trifluoromethanesulfonic acid (CF3SO3H, TfOH). Tropinone (6) and quinuclidone (7) also react in good yields with benzene in TfOH
to give the condensation products (13 and 14). Ketal and acetal derivatives also give condensation
products (8 and 24) upon reaction with C6H6 in TfOH. The conversion of 3g to 11 is sensitive to
both acid quantity and acid strength; a mechanism is proposed for the conversion that invokes
dicationic intermediates.