Addition of Alcohols Onto Electron-Deficient Heteroarenium Salts: A Reversible Covalent Bonding Process under Basic Conditions

The reversible addition of benzyl alcohol onto heteroarenium salts under basic conditions was studied. Fine-tuning of the nature of the arenium and substituents allowed the discovery of a range of pyrimidinium substrates that can undergo C6-selective alcohol addition. Crossover experiments were also performed to confirm the addition elimination equilibrium under basic conditions.