Recent advances in the synthesis of γ-keto sulfones

Abstract

As an important class of sulfone compounds, γ-keto sulfones have attracted widespread attention from chemists due to their anticoagulant, antibacterial, and anticancer activities. In this article, the synthesis of γ-keto sulfones over the period from 2020 to the present will be discussed, and the related reaction mechanisms will also be discussed. Several approaches will be reviewed and they can be divided into (i) direct sulfonylation/acylation of alkenes via radical Michael addition, (ii) sulfonylation of α,β-unsaturated or β,γ-unsaturated ketones with sulfonylation reagents, (iii) hydroacylation of vinylsulfones, (iv) ring-opening sulfonylation of cyclopropanols, (v) 1,2-migration of allyl or propargyl alcohols, (vi) sulfonylation of allenic carbonyl compounds, (vii) sulfonylation of sulfoxonium ylides and (viii) hydrogenation of β sulfonyl-α,β-unsaturated ketones. From the perspective of reaction mechanism, in the process of synthesizing γ-keto sulfones, the reaction system produced some key intermediates such as sulfonyl radicals, sulfinate anions, γ-keto sulfonates, γ-keto sulfonyl radicals, β-keto radicals, acyl radicals, etc., which played a decisive role in the success of the reaction.