Cyclic Vinyl(aryl)iodonium Salts: Synthesis and Reactivity

A convenient, highly regioselective synthesis of five-membered cyclic vinyl­(aryl)­iodonium salts directly from β-iodostyrenes is presented. An X-ray crystal structure confirms the identity of these heterocycles. These λ³-iodanes can be converted rapidly into functionalized arylacetylenes by treatment with mild base or undergo S_NV reactions with nonbasic nucleophiles.