The iron(III) chloride-mediated 1,4-addition of mercaptans to α,β-unsaturated ketones and esters under solvent free conditions

The 1,4-addition of various thiols to alpha,beta-unsaturated ketones was completed rapidly in the presence of a catalytic amount (2-3 mol %) of anhydrous iron(III) chloride under solvent free conditions and an air atmosphere. Anhydrous iron(III) chloride is more active than that of other ferric salts. With more reactive and/or less steric reagents (1a-c and/or 2a-2c), expeditious conditions (short reaction times at room temperature) could be employed. With less reactive and/or steric reagents (1d-g and/or 2d-e), a slight increase in reaction time was required, but high yields were obtained. The FeCl3 catalyst causes preferential interactions with alpha,beta-unsaturated ketones present in the reaction. (c) 2006 Published by Elsevier Ltd.