Direct Access to Fluorene by Successive C?O/C?H Bond Activations of 2?Phenylbenzyl Ester

摘要

Catalytic formation of fluorene has been achieved from 2-phenylbenzyl trifluoroacetate via successive C?O and C?H bond cleavage reactions by Pd(OAc)_2/PPh_3 in 97% yield. This reaction involves the oxidative addition of ester to give (carboxylato)(2-phenylbenzyl)palladium(II) species and deprotonation from the 2-phenylbenzyl group by the cleaved carboxylato group via an internal electrophilic substitution mechanism.