Zirconium(IV) chloride as a new, highly efficient, and reusable catalyst for acetylation of phenols, thiols, amines, and alcohols under solvent-free conditions.

Abstract

Zirconium(IV) chloride has been found to be a new, highly efficient, and reusable catalyst for acetylation of structurally diverse phenols, thiols, amines, and alcohols under solvent-free condtions. Acetylation of sterically hindered and electron deficient phenols is achieved in excellent yields with stoichiometric amounts of Ac2O at room temperature. Acid-sensitive alcohols undergo acetylation with excellent chemoselectivity without competitive side reactions such as dehydration or rearrangement. The mild Lewis acid property of the catalyst enables the acetylation to be carried out with optically active substrates without any detrimental effect on the optical purity.