A Class of Phase-Transfer Catalyst with Interionic Strain: Insight into the Bonding of Disubstituted N- vs Carbene-Stabilized NI‑Centered Cations

The straightforward synthesis of a class of nitrogen-based phase-transfer catalysts (PTCs) having markedly dissociated anions due to interionic donor–donor “ion pair strain” and use for catalyzing benzylation and benzylic fluorination is reported. Provided also is insight into the bonding of disubstituted N- vs so-called divalent carbene-stablized NI-centered cations and the unprecedented finding of a cyclopropenium based C–H···πaryl interaction.