One-pot preparation of hydroxylated potassium organotrifluoroborates and subsequent Jones oxidation to potassium organocarbonyltrifluoroborates

Abstract

Alcohol-containing potassium organotrifluoroborates as starting reagents were prepared from their corresponding dibromobenzenes through a sequential one-pot reaction. The oxidation reactions of these substrates, which were carried out using 3.0 equiv of 8 N Jones reagent in acetone at 0 degrees C, provided a high yield of the desired carbonyl-functionalized compounds. In addition, the cross-coupling reactions of these organocarbonyltrifluoroborates were successfully performed in the presence of 3 mol % of Pd (PPh3)(4) catalyst at 100 degrees C. (C) 2010 Elsevier Ltd. All rights reserved.