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

Abstract

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.

Keywords

heteroarenium salts - alcohols - reversible addition - basic conditions

Publication History

Received: 07 September 2022

Accepted after revision: 02 January 2023

Accepted Manuscript online:
02 January 2023

Article published online:
25 January 2023

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