A myriad of nucleophiles for the Michael-type reaction of soft nucleophiles with alkynyliodonium species have been explored in the chemical literature. One intriguing set of nucleophiles, the alkylamines, have not been explored. In the presented work we utilized a highly stable class of alkynyliodonium species created using 1H-1-hydroxy-1,2,3-benziodoxathiole 3,3-dioxide (HBI) to explore this reaction. These 1H-1-alkynyl-1,2,3-benziodoxathiole 3,3-dioxides are obtainable in high yields by treating terminal alkynes with an aryl or alkyl substituent with HBI in dichloromethane in the presence of trifluoroacetic anhydride at room temperature. Subsequent treatment of the alkynyliodonium compounds with methylamine under aqueous conditions leads to the formation of enamine and alkenimine (C=C=N) intermediary compounds which are rapidly hydrolyzed under the reaction conditions. In all cases, the reduced 2-iodobenzene sulfonic acid is readily separated from the reaction mixture by simple liquid-liquid extraction techniques and can be recycled and reused.

Study of the reaction of the methylamine nucleophile with 1H-1-alkynyl-1,2,3-benziodoxathiole 3,3-dioxides

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