Cyclic Vinyl(aryl)iodonium Salts: Synthesis and Reactivity

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 treatme...

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Veröffentlicht in:Organic letters 2019-09, Vol.21 (17), p.6936-6939
Hauptverfasser: Kepski, Konrad, Rice, Craig R, Moran, Wesley J
Format: Artikel
Sprache:eng
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Zusammenfassung: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 SNV reactions with nonbasic nucleophiles.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02540