Sulfonic acid based cation-exchange resin: A novel proton source for one-pot diazotization-iodination of aromatic amines in water

Victor D. Filimonov, Nadya I. Semenischeva, Elena A. Krasnokutskaya, Alexei N. Tretyakov, Yun Hwang Ho, Ki Whan Chi

The Kizhner Research Center

Research output: Contribution to journal › Article

Abstract

A convenient and simple one-pot method for the preparation of iodoarenes at room temperature has been developed, by sequential diazotization-iodination of aromatic amines with NaNO₂/KI in the presence of a sulfonic acid based cation-exchange resin in water. This inexpensive, noncorrosive and eco-friendly synthetic route is general in nature and allows for the preparation of iodoarenes with an electron-donating or -withdrawing group in various positions from the corresponding amines in 50-98% yields.

Original language	English
Pages (from-to)	185-187
Number of pages	3
Journal	Synthesis
Issue number	2
DOIs	https://doi.org/10.1055/s-2007-990950
Publication status	Published - 17 Jan 2008

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Keywords

Aromatic amines
Cation-exchange resin
Diazotization
Iodoarenes
Potassium iodide
Sodium nitrite

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Cite this

Filimonov, V. D., Semenischeva, N. I., Krasnokutskaya, E. A., Tretyakov, A. N., Ho, Y. H., & Chi, K. W. (2008). Sulfonic acid based cation-exchange resin: A novel proton source for one-pot diazotization-iodination of aromatic amines in water. Synthesis, (2), 185-187. https://doi.org/10.1055/s-2007-990950

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abstract = "A convenient and simple one-pot method for the preparation of iodoarenes at room temperature has been developed, by sequential diazotization-iodination of aromatic amines with NaNO2/KI in the presence of a sulfonic acid based cation-exchange resin in water. This inexpensive, noncorrosive and eco-friendly synthetic route is general in nature and allows for the preparation of iodoarenes with an electron-donating or -withdrawing group in various positions from the corresponding amines in 50-98{\%} yields.",

keywords = "Aromatic amines, Cation-exchange resin, Diazotization, Iodoarenes, Potassium iodide, Sodium nitrite",

author = "Filimonov, {Victor D.} and Semenischeva, {Nadya I.} and Krasnokutskaya, {Elena A.} and Tretyakov, {Alexei N.} and Ho, {Yun Hwang} and Chi, {Ki Whan}",

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AU - Filimonov, Victor D.

AU - Semenischeva, Nadya I.

AU - Krasnokutskaya, Elena A.

AU - Tretyakov, Alexei N.

AU - Ho, Yun Hwang

AU - Chi, Ki Whan

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KW - Cation-exchange resin

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KW - Iodoarenes

KW - Potassium iodide

KW - Sodium nitrite

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Access to Document

10.1055/s-2007-990950