A green procedure for the diazotization-iodination of aromatic amines under aqueous, strong-acid-free conditions

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27 Citations (Scopus)

Abstract

A convenient and mild one-pot method for the synthesis of iodoarenes in high yields by the sequential diazotization-iodination of aromatic amines with a reusable polymeric diazotization agent in the presence of p-toluenesulfonic acid at room temperature in water was developed. The method is general and is the greenest alternative of the known diazotization-iodination methods. The method is also effective for the preparation of 1H-benzo[d][1,2,3]triazole and benzo[d][1,2,3]thiadiazole.

Original languageEnglish
Pages (from-to)2154-2158
Number of pages5
JournalSynthesis
Issue number13
DOIs
Publication statusPublished - 2011

Fingerprint

Thiadiazoles
Triazoles
Amines
Acids
Water
Temperature
4-toluenesulfonic acid

Keywords

  • amines
  • diazotization
  • halogenation
  • heterocycles
  • iodination

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

Cite this

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title = "A green procedure for the diazotization-iodination of aromatic amines under aqueous, strong-acid-free conditions",
abstract = "A convenient and mild one-pot method for the synthesis of iodoarenes in high yields by the sequential diazotization-iodination of aromatic amines with a reusable polymeric diazotization agent in the presence of p-toluenesulfonic acid at room temperature in water was developed. The method is general and is the greenest alternative of the known diazotization-iodination methods. The method is also effective for the preparation of 1H-benzo[d][1,2,3]triazole and benzo[d][1,2,3]thiadiazole.",
keywords = "amines, diazotization, halogenation, heterocycles, iodination",
author = "Trusova, {Marina E.} and Krasnokutskaya, {Elena A.} and Postnikov, {Pavel S.} and Younghwa Choi and Chi, {Ki Whan} and Filimonov, {Victor D.}",
year = "2011",
doi = "10.1055/s-0030-1260046",
language = "English",
pages = "2154--2158",
journal = "Synthesis",
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T1 - A green procedure for the diazotization-iodination of aromatic amines under aqueous, strong-acid-free conditions

AU - Trusova, Marina E.

AU - Krasnokutskaya, Elena A.

AU - Postnikov, Pavel S.

AU - Choi, Younghwa

AU - Chi, Ki Whan

AU - Filimonov, Victor D.

PY - 2011

Y1 - 2011

N2 - A convenient and mild one-pot method for the synthesis of iodoarenes in high yields by the sequential diazotization-iodination of aromatic amines with a reusable polymeric diazotization agent in the presence of p-toluenesulfonic acid at room temperature in water was developed. The method is general and is the greenest alternative of the known diazotization-iodination methods. The method is also effective for the preparation of 1H-benzo[d][1,2,3]triazole and benzo[d][1,2,3]thiadiazole.

AB - A convenient and mild one-pot method for the synthesis of iodoarenes in high yields by the sequential diazotization-iodination of aromatic amines with a reusable polymeric diazotization agent in the presence of p-toluenesulfonic acid at room temperature in water was developed. The method is general and is the greenest alternative of the known diazotization-iodination methods. The method is also effective for the preparation of 1H-benzo[d][1,2,3]triazole and benzo[d][1,2,3]thiadiazole.

KW - amines

KW - diazotization

KW - halogenation

KW - heterocycles

KW - iodination

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