Phase-Transfer Catalyzed O-Silyl Ether Deprotection Mediated by a Cyclopropenium Cation

The use of a cyclopropenium cation as a phase-transfer catalyst for O-silyl ether deprotection is reported. Mechanistic insight into this deprotection methodology derived by linear free-energy relationships (LFER), quantum theory of atoms in molecules (QTAIM), and density functional theory (DFT) calculations are also provided.