Zirconocene bis(perfluorooctanesulfonate)s-catalyzed acylation of alcohols, phenols, thiols, and amines under solvent-free conditions

Air-stable zirconocene bis(perfluorooctanesulfonate)s [CP2Zr(OPf)(2), OPf = OSO2CsF17] showing high Lewis acidity and high thermal stability was prepared by reacting Cp2ZrCl2 with AgOPf, and examined as a catalyst for acylation reactions. It was found that in the acetylation of various alcohols, phenols, thiols, and amines by equimolar of acetic anhydride, Cp2Zr(OPf)(2) exhibits high activity and selectivity to desired products under mild and solvent-free conditions. In the acylation of 2-phenylethanol across various acylating reagents, it also shows good catalytic efficiency. In a test of ten cycles, Cp2Zr(OPf)(2) shows little loss of activity. The results afford a general and efficient method for the acylation of alcohols, phenols, thiols, and amines using zirconium bis(perfluorooctanesulfonate) as catalyst. (c) 2009 Elsevier B.V. All rights reserved.