Cyclic Vinyl(aryl)iodonium Salts: Synthesis and Reactivity

Konrad Kepski; Craig Rice; Wesley Moran

doi:10.1021/acs.orglett.9b02540

Cyclic Vinyl(aryl)iodonium Salts: Synthesis and Reactivity

Konrad Kepski, Craig Rice, Wesley Moran

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

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 S_NV reactions with nonbasic nucleophiles.

Original language	English
Pages (from-to)	6936-6939
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	17
Early online date	27 Aug 2019
DOIs	https://doi.org/10.1021/acs.orglett.9b02540
Publication status	Published - 6 Sep 2019

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title = "Cyclic Vinyl(aryl)iodonium Salts: Synthesis and Reactivity",

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.",

keywords = "Hypervalent iodine, Heterocycle",

author = "Konrad Kepski and Craig Rice and Wesley Moran",

year = "2019",

month = sep,

day = "6",

doi = "10.1021/acs.orglett.9b02540",

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journal = "Organic Letters",

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T1 - Cyclic Vinyl(aryl)iodonium Salts

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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U2 - 10.1021/acs.orglett.9b02540

DO - 10.1021/acs.orglett.9b02540

M3 - Article

VL - 21

SP - 6936

EP - 6939

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 17

ER -

Cyclic Vinyl(aryl)iodonium Salts: Synthesis and Reactivity

Abstract

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