Synthesis and reactivity of donor stabilized thionylium (SO 2+ ) dications.

Robust mono-, di-, and tridentate base-stabilized thionylium (SO 2+ ) dications were synthesized from the treatment of SOCl 2 with Me 3 SiO 3 SCF 3 and pyridine-based ligands. Computational and experimental data are consistent with Lewis acidities comparable to BF 3 and PF 5 and these compounds were shown to activate C-F bonds of fluoroalkanes. These dications also react with Ph 3 PO and CuO to effect O 2- abstraction in an overall redox-neutral deoxygenation process driven by the evolution of SO 2 .