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

doi:10.1055/s-2006-958936

PAPER

A New, One-Step, Effective Protocol for the Iodination of Aromatic and Heterocyclic Compounds via Aprotic Diazotization of Amines

Elena A. Krasnokutskaya*^a, Nadya I. Semenischeva^a, Victor D. Filimonov^a, Paul Knochel^b
^a Department of Organic Chemistry, Tomsk Polytechnic University, 634050 Tomsk, Russian Federation
Fax: +7(3822)563861; e-Mail: e_krasnokutskaya@mail.ru;
^b Department Chemie, Ludwig-Maximilians-University, Butenandtstrasse 5-13, 81377 Munich, Germany
Fax: +49(89)218077680; e-Mail: Paul.Knochel@cup.uni-muenchen.de;

Abstract

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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.

Key words

aromatic iodides - aromatic amines - diazotization - potassium iodide - sodium nitrite

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