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.

Automated summary

The reversible addition of benzyl alcohol onto heteroarenium salts under basic conditions was investigated. By fine-tuning the nature of the arenium and substituents, a range of pyrimidinium substrates capable of undergoing C6-selective alcohol addition was discovered. Crossover experiments were conducted to confirm the addition elimination equilibrium under basic conditions.