Electrochemical pinacol coupling of aromatic carbonyl compounds in a [BMIM][BF4]–H2O mixture

Abstract

The electrochemical pinacol coupling reactions of aromatic carbonyl compounds were carried out using an 80% [BMIM][BF₄]–H₂O mixture as the electrolytic medium. The corresponding diols were obtained in good to excellent yields with moderate diastereoselectivity. The stereoselectivity can be explained using the strongly-bound ion-pairs formed between the imidazolium cation and the radical anions of the carbonyl compounds. The ionic liquid replaces both organic solvents and supporting electrolytes generally used in the electrosynthetic method. The electrolytic medium can be recycled and successfully reused at least in five consecutive reactions.