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

Elena A. Krasnokutskaya, Nadya I. Semenischeva, Victor D. Filimonov, Paul Knochel

The Kizhner Research Center

Research output: Contribution to journal › Article

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

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Keywords

Aromatic amines
Aromatic iodides
Diazotization
Potassium iodide
Sodium nitrite

ASJC Scopus subject areas

Organic Chemistry

Cite this

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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AU - Filimonov, Victor D.

AU - Knochel, Paul

PY - 2007/1/4

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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.

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KW - Diazotization

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KW - Sodium nitrite

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Access to Document

10.1055/s-2006-958936