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

Sulfones in heterocyclic synthesis: advances in the chemistry of phenyl sulfonylacetophenone 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

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

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Publisher
Springer Netherlands
Copyright
Copyright © 2017 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-017-2869-8
Publisher site
See Article on Publisher Site

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.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Feb 6, 2017

References

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