Iodonium transfer reagents such as phenyl(cyano)iodonium triflate (Stang’s reagent) can be used to activate propargylic alcohols that contain a pendant aromatic ring. Once activated, a domino sequence ensues and involves intramolecular trapping of the intermediate cation and dehydration to afford crystalline naphthyl(aryl)iodonium salts. Results of studies on structure, stoichiometry and mechanism will be presented.

Electrophilic activation and domino reaction of arylated propargylic alcohols toward naphthyl(aryl)iodonium salts

254th National Meeting (2017)

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