Ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones

Abstract

A novel ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones is described. The process proceeded smoothly under metal-free conditions with high stereoselectivity and good functional group tolerance. The reaction mechanism was revealed to proceed through a domino reaction of oxidation and elimination after the radical addition to alkenes.

Eosin Y (EY) Photoredox‐Catalyzed Sulfonylation of Alkenes: Scope and Mechanism

“…[10] Vinyl methyl sulfone preparation, to date, requires copper-catalyzed reactions of alkynes [11] or alkenes [12] with DMSO,o rt he ammoniumi odide-induceds ulfonylation of olefinsw ith DMSO. [13] Herein, we report av isible-light-mediated, metal-free synthesis of alkyl and heteroaryl vinyl sulfones from alkyl or heteroaryl sulfinates and alkenesu sing green light, the organic dyee osin Y( EY) as photocatalyst and nitrobenzene or air as the terminal oxidant (Scheme 1b). Alternatively,t he oxidative coupling reactionc an be combined with ahydrogen-evolution reaction.…”

Direct Assembly of Polysubstituted Furans via C(sp3)−H Bond Functionalization by Using Dimethyl Sulfoxide as a Dual Synthon

“…At low temperature, the acetophenone could not fully converted to the product (entry 12). It is worth noting that the yield of product was decreased when changing the amount of DMSO and K 2 S 2 O 8 (entries [13][14][15][16].…”

“…[7] Antonchick's group demonstrated a furan synthesis via Cu-catalyzed C(sp 3 )ÀH functionalization of aryl methyl ketones with alkynes (Scheme 1b). [11] In the past decades, DMSO has also been widely utilized as a single synthon as a source for units such as O, [12] Me, [13] SMe, [14] SOMe, [15] SO 2 Me, [16] MeSCH 2 , [17] MeSOCH 2 , [18] and CN [19] for incorporation into target molecules. [9] Recently, the Wu group reported an I 2 / Cu(NO 3 ) 2 · 3H 2 O mediated triple C(sp 3 )ÀH bond functionalization reaction of aryl methyl ketones and rongalite.…”

“…Dimethyl sulfoxide (DMSO) is one of the most commonly used, inexpensive, and less toxic solvents in chemical transformations. [11] In the past decades, DMSO has also been widely utilized as a single synthon as a source for units such as O, [12] Me, [13] SMe, [14] SOMe, [15] SO 2 Me, [16] MeSCH 2 , [17] MeSOCH 2 , [18] and CN [19] for incorporation into target molecules. However, to the best of our knowledge, the application of DMSO as a dual synthon in the construction of the furan scaffold has not yet been reported.…”

Silver‐Catalyzed Denitrative Sulfonylation of β‐Nitrostyrenes: A Conve­nient Approach to (E)‐Vinyl Sulfones

“…Although these reactions are efficient, the use of poisonous metals and expensive ligands makes them unsuitable from a synthetic point of view. Li and co‐workers developed the ammonium iodide induced sulfonylation of alkenes with DMSO 20. However, this method is limited to the synthesis of only vinyl methyl sulfones.…”