PAPER	Synthesis 2004: 111-115   DOI: 10.1055/s-2003-44362
© Georg Thieme Verlag Stuttgart · New York
Copper(II) Tetrafluoroborate-Catalyzed Acetylation of Phenols, Thiols, Alcohols­, and Amines
Asit K. Chakraborti*, Rajesh Gulhane, Shivani
National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, Punjab - 160062, India Fax: +91(172)2214692; e-Mail: akchakraborti@niper.ac.in;
Received 27 August 2003

Abstract

Copper(II) tetrafluoroborate efficiently catalyzes acetyl­ation of structurally diverse phenols, alcohols, thiols, and amines with stoichiometric amounts of Ac₂O under solvent-free conditions at room temperature. Acid-sensitive alcohols are smoothly acetylated without competitive side reactions. The reaction is influenced by the steric and electronic factors associated with the substrate as well as the anhydride. Acetylation of a sterically hindered substrate requires excess of anhydride and longer time. Acylation with less electrophilic anhydrides affords poor to moderate yields.

Key words

acetylation - copper(II) tetrafluoroborate - solvent-free