Sulfones in heterocyclic synthesis: advances in the chemistry of phenyl sulfonylacetophenone

Abstract

The present review provides a survey on the structural features, synthetic methodologies, and reactions of phenyl sulfonylacetophenone, considered to be one of the most important synthons in the field of synthetic organic chemistry. β-Ketosulfone is an active C–H acid which has been widely used as a nucleophile in many organic transformations. It has been used for synthesis of five- and six-membered ring systems containing one or two heteroatoms. In addition, it has been used as a starting material for synthesis of fused heterocycles, cyclopropane, cyclopentene, and cyclohexanone derivatives. β-Ketosulfone has been used for synthesis of γ- and δ-ketosulfones, 1,4-diketones, amides, ethers, and substituted benzene derivatives due to its high synthetic importance. It is a reactive intermediate in electrophilic reactions such as halogenation, alkylation, arylation, heteroarylation, and coupling reactions, and is involved in other types of reaction such as Diels–Alder condensation with aldehydes and desulfonylation. The mechanistic pathways of these reactions and their important synthetic applications are discussed herein.