A new, one-step, effective protocol for the iodination of aromatic and heterocyclic compounds via aprotic diazotization of amines

Abstract

We have developed a convenient one-step preparation of aromatic and some heterocyclic iodides by the sequential diazotization-iodination of the aromatic amines with a KI/NaNO₂/p-TsOH system in acetonitrile at room temperature. This method has general character and allows aryl iodides with either donor or acceptor substituents in various positions to be obtained from the corresponding amines in 50-90% yield.

Original language	English
Pages (from-to)	81-84
Number of pages	4
Journal	Synthesis
Issue number	1
DOIs	https://doi.org/10.1055/s-2006-958936
Publication status	Published - 4 Jan 2007

Keywords

Aromatic amines
Aromatic iodides
Diazotization
Potassium iodide
Sodium nitrite

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-2006-958936

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Krasnokutskaya, E. A., Semenischeva, N. I., Filimonov, V. D., & Knochel, P. (2007). A new, one-step, effective protocol for the iodination of aromatic and heterocyclic compounds via aprotic diazotization of amines. Synthesis, (1), 81-84. https://doi.org/10.1055/s-2006-958936

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abstract = "We have developed a convenient one-step preparation of aromatic and some heterocyclic iodides by the sequential diazotization-iodination of the aromatic amines with a KI/NaNO2/p-TsOH system in acetonitrile at room temperature. This method has general character and allows aryl iodides with either donor or acceptor substituents in various positions to be obtained from the corresponding amines in 50-90% yield.",

keywords = "Aromatic amines, Aromatic iodides, Diazotization, Potassium iodide, Sodium nitrite",

author = "Krasnokutskaya, {Elena A.} and Semenischeva, {Nadya I.} and Filimonov, {Victor D.} and Paul Knochel",

year = "2007",

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T1 - A new, one-step, effective protocol for the iodination of aromatic and heterocyclic compounds via aprotic diazotization of amines

AU - Krasnokutskaya, Elena A.

AU - Semenischeva, Nadya I.

AU - Filimonov, Victor D.

AU - Knochel, Paul

PY - 2007/1/4

Y1 - 2007/1/4

N2 - We have developed a convenient one-step preparation of aromatic and some heterocyclic iodides by the sequential diazotization-iodination of the aromatic amines with a KI/NaNO2/p-TsOH system in acetonitrile at room temperature. This method has general character and allows aryl iodides with either donor or acceptor substituents in various positions to be obtained from the corresponding amines in 50-90% yield.

AB - We have developed a convenient one-step preparation of aromatic and some heterocyclic iodides by the sequential diazotization-iodination of the aromatic amines with a KI/NaNO2/p-TsOH system in acetonitrile at room temperature. This method has general character and allows aryl iodides with either donor or acceptor substituents in various positions to be obtained from the corresponding amines in 50-90% yield.

KW - Aromatic amines

KW - Aromatic iodides

KW - Diazotization

KW - Potassium iodide

KW - Sodium nitrite

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