Transition-metal-free NaI-mediated reaction of aryl sulfonyl chloride with alkynes: Synthesis of (E)-β-iodovinyl sulfones

Advances in Vinyl Sulfone Catalyzed Synthesis: Methods, Mechanisms and Perspectives

“…Chen and co-workers extended molecular iodine to iodide salts to mediate radical addition reactions between aryl sulfonyl chlorides and alkynes (Scheme 12). [62] Under the condition of 2 equiv. of NaI and heating, p-toluenesulfonyl chloride will be substituted to generate p-toluenesulfonyl iodide.…”

“…Synthesis of vinyl sulfones mediated by Ionic iodine. [62] Scheme 13. Synthesis of vinyl sulfones mediated by NIS.…”

Recent trends in the synthesis and applications of β-iodovinyl sulfones: a decade of progress

“…Using a combination of aryl sulfonyl chlorides 5 and sodium iodide (NaI) was suitable in the 1,2-iodosulfonylation of alkynes 1 in the presence of NaOAc in acetic acid at 80 °C gave ( E )-β-iodovinyl sulfones 3 (Scheme 21, method A). Li, Jiang, and co-workers 38 explored electronically diverse substitutions on the phenyl ring of terminal alkynes and found that they reacted smoothly with tosyl chloride to furnish the corresponding ( E )-β-iodovinyl sulfones. Additionally, a series of aryl sulfonyl chlorides bearing electron-donating and electron-withdrawing substituents were smoothly coupled with phenylacetylene to obtain the desired vinyl sulfonated products in high yields.…”

Synthesis of β-iodovinyl sulfonesviadirect photoinitiated difunctionalization of internal alkynes

“…[17][18][19][20][21][22] The development of methods for synthesis of sulfones has recently attracted the attention of many researchers. [23][24][25][26][27][28] One of the most efficient methods for creating a C-SO 2 bond to obtain vinyl sulfones is the alkyne sulfonylation reaction is the addition of a sulfonyl radical to an alkyne.…”