Advances in Oxosulfonylation Reaction

Abstract

Oxosulfonylation is a difunctionalization protocol where oxo and sulfonyl groups are introduced in one step to construct ketosulfones and Nacylsulfonamides from simple and readily accessible reagents. The development of oxosulfonylation methods has gained significant attention due to their importance in organic and medicinal chemistry. This review article provides a brief and concise overview of the current status and latest methodologies using green oxidant and sulfonyl sources for oxosulfonylation reactions developed in the last two decades.

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

“…115 At the same time, Felpin and Landais reported using inexpensive Pd/C-catalyst for the sulfonylation of allylic acetates with sodium p-toluenesulnate in water (Scheme 60B). 116 The linear allylic acetate reacted smoothly with only 1 mol% of Pd/C; however, the branched allylic acetates required 5 mol% of Pd/ C in the presence of Ph 3 P. More interestingly, the chiral allylic acetate (18) was successfully sulfonylated with sodium p-tolue-nesulnate and provided the desired linear allyl sulfone (19) along with branched sulfone (20) as shown in Scheme 60.…”

“…16 Among the C-S bonds forming reactions of sodium sulnates, vinyl sulfones, 17,18 allylic sulfones and b-keto sulfones are formed. 19,20 These types of organosulfur compounds are broadly used in different pharmaceutical applications, which may lead to forthcoming medicinal therapies. 21 Several attractive features of sodium sulnates have been recently envisioned: the S-centered sulfonyl radical-triggered ringclosing sulfonylation, multicomponent reactions of sodium sulnates, and remote site-selective C-H sulfonylation.…”

Hydroxysulfonylation of alkenes: an update

“…Of note, we have not discussed oxosulfonylation reactions, since it has recently been described in another publication. 14 …”

Chemoenzymatic Oxosulfonylation‐Bioreduction Sequence for the Stereoselective Synthesis of β‐Hydroxy Sulfones

“…Their straightforward synthesis can be accomplished through different chemical routes, probably the most useful ones being: (a) the acylation of methyl sulfones; (b) reaction between generated enolates with sulfonyl iodides; (c) oxidation of β‐keto sulfides; and the reaction of sulfinate salts with (d) α‐halo ketones or (e) either alkynes or alkenes under aerobic conditions and metal‐ or photo‐catalysis (Scheme 1). In this context, the oxosulfonylation of multiple C−C bonds has received special attention due to its high atom‐economy, simple set‐up, and possibility to carry out a difunctionalization of alkynes in both aqueous and organic media [2] . The presence of the sulfone moiety, α‐acidic protons at the methylene group, and the carbonyl function provide β‐keto sulfones with multiple synthetic possibilities, the asymmetric reduction of the carbonyl group representing the simple manner to provide access to optically active β‐hydroxy sulfones.…”