Synthesis of (E)-β-iodovinyl sulfones via DTBP/I₂ promoted difunctionalization of alkynes with sodium benzenesulfinates

Recent Advances in Iodine‐Promoted C−S/N−S Bonds Formation

“… [26b] Similarly, Zhao and co‐workers reported an iodine‐promoted strategy to construct β‐iodovinyl sulfones via difunctionalization of alkynes with sodium benzenesulfinates under mild and environmentally benign conditions (Scheme 3 c). [26c] Then, Liu and co‐workers revealed an iodine‐promoted approach to the preparation of vinyl sulfones with sodium sulfinates via tandem radical reactions (Scheme 3 d). [26d] Additionally, Yallapragada and co‐workers developed an effective iodine‐promoted access to synthesize vinyl sulfones with p ‐toluenesulfonylmethyl isocyanide (TosMIC) as a novel sulfur sources under benign conditions [26e] …”

Pyrimidine Nucleosides with a Reactive (β-Chlorovinyl)sulfone or (β-Keto)sulfone Group at the C5 Position, Their Reactions with Nucleophiles and Electrophiles, and Their Polymerase-Catalyzed Incorporation into DNA

“… 28 − 30 The (β-halo)vinyl sulfones are gaining attention as a new class of reactive sulfones. 31 Recent synthetic developments include metal-free stereoselective E -iodosulfonylation of internal alkynes with sodium phenyl sulfinate and iodine to provide tetrasubstituted olefins, 32 di- t -butyl peroxide/I 2 -promoted difunctionalization of alkynes with sodium benzenesulfinates to give ( E )-β-iodovinyl sulfones, 33 and multicomponent reactions with insertion of sulfur dioxide. 34 The application of (α-halo)vinyl sulfones to organic synthesis as well as nucleoside and medicinal chemistry is also documented.…”

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

“…Simultaneously, Bi et al reported a simple protocol to synthesize ( E )-β-iodovinyl sulfones via molecular iodine and di- tert -butyl peroxide (DTBP)-promoted iodosulfonylation of alkynes with sodium sulfinates under mild conditions ( Scheme 125 ). 189 Various aryl- and alkyl-acetylenes were successfully explored with sodium arylsulfinates or methanesulfinate to provide a series of functionalized ( E )-β-iodovinyl sulfones in moderate to high yields. The electron-rich groups on phenylacetylene gave high yields as compared with electron-poor groups on phenylacetylene, which significantly decreased the yields.…”