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.

Original language	English
Pages (from-to)	2154-2158
Number of pages	5
Journal	Synthesis
Issue number	13
DOIs	https://doi.org/10.1055/s-0030-1260046
Publication status	Published - 2011

Keywords

amines
diazotization
halogenation
heterocycles
iodination

ASJC Scopus subject areas

Organic Chemistry
Catalysis

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10.1055/s-0030-1260046

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@article{c830a177296b4ce1b234983957a3f544,

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",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "13",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=79959379432&partnerID=8YFLogxK

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U2 - 10.1055/s-0030-1260046

DO - 10.1055/s-0030-1260046

M3 - Article

AN - SCOPUS:79959379432

SP - 2154

EP - 2158

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 13