Ferric chloride-catalyzed decarboxylative alkylation of β-keto acids with benzylic alcohols

Abstract

β-Keto acids are unstable to heat, acids, and bases, and have rarely been employed as carbon nucleophiles for the formation of carbon-carbon bonds. In this context, an efficient decarboxylative alkylation reaction of β-keto acids with benzylic alcohols has been developed, for the first time, through sequential cleavage of carbon-oxygen and carbon-carbon bonds. In the presence of 10 mol% of ferric chloride, a range of β-keto acids smoothly undergo decarboxylative alkylation with benzylic alcohols to give structurally diverse unsymmetric ketones in moderate to excellent yields and with extremely high regioselectivity. Preliminary mechanistic studies indicate that the reaction proceeds through an S N1 alkylation followed by decarboxylation. © 2012 The Author(s).