Sulfones in heterocyclic synthesis: advances in the chemistry of phenyl sulfonylacetophenone (original) (raw)

2017, Research on Chemical Intermediates

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. b-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 sixmembered 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. b-Ketosulfone has been used for synthesis of cand d-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.