Cyclic Vinyl(aryl)iodonium Salts

Synthesis and Reactivity

Konrad Kepski, Craig Rice, Wesley Moran

Research output: Contribution to journalArticle

Abstract

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.
Original languageEnglish
Pages (from-to)6936-6939
Number of pages4
JournalOrganic Letters
Volume21
Issue number17
Early online date27 Aug 2019
DOIs
Publication statusPublished - 6 Sep 2019

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Nucleophiles
nucleophiles
reactivity
Salts
Crystal structure
X-Rays
salts
X rays
crystal structure
synthesis
x rays

Cite this

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abstract = "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.",
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Cyclic Vinyl(aryl)iodonium Salts : Synthesis and Reactivity. / Kepski, Konrad; Rice, Craig; Moran, Wesley.

In: Organic Letters, Vol. 21, No. 17, 06.09.2019, p. 6936-6939.

Research output: Contribution to journalArticle

TY - JOUR

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T2 - Synthesis and Reactivity

AU - Kepski, Konrad

AU - Rice, Craig

AU - Moran, Wesley

PY - 2019/9/6

Y1 - 2019/9/6

N2 - 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.

AB - 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.

KW - Hypervalent iodine

KW - Heterocycle

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