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Synthesis 2011(13): 2154-2158  
DOI: 10.1055/s-0030-1260046
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Green Procedure for the Diazotization-Iodination of Aromatic Amines under Aqueous, Strong-Acid-Free Conditions

Marina E. Trusovaa, Elena A. Krasnokutskayaa, Pavel S. Postnikova, Younghwa Choib, Ki-Whan Chi*b, Victor D. Filimonov*a
a Department of Organic Chemistry, National Research Tomsk Polytechnic University, Tomsk 634050, Russian Federation
e-Mail: filimonov@tpu.ru;
b Department of Chemistry, University of Ulsan, Ulsan 680-749, Republic of Korea
e-Mail: kwchi@ulsan.ac.kr;
Further Information

Publication History

Received 7 April 2011
Publication Date:
13 May 2011 (online)

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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.

Key words

diazotization - halogenation - iodination - heterocycles - amines

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10

For several examples, the resulting diazonium tosylates can be partially isolated from the aqueous solution by extraction with ethyl acetate, followed by pouring the organic solution in diethyl ether. Properties and spectral data of these salts were identical to those previously obtained by diazotization in acetic acid.8