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, Ho Yun Hwang, Ki-Whan Chi

*Department of Organic Chemistry, Tomsk Polytechnic University, 634050 Tomsk, Russia, Email: filimonovtpu.ru

V. D. Filimonov, N. I. Semenischeva, E. A. Krasnokutskaya, A. N. Tretyakov, H. Y. Hwang, K.-W. Chi, Synthesis, 2008, 185-187.

DOI: 10.1055/s-2007-990950

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Abstract

Convenient and simple, sequential diazotization-iodination of aromatic amines with NaNO₂/KI in the presence of a sulfonic acid based cation-exchange resin in water is an inexpensive, noncorrosive and eco-friendly synthetic route, that allows the preparation of various electron-rich and deficient iodoarenes in good yields.

see article for more examples

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Unusually Stable, Versatile, and Pure Arenediazonium Tosylates: Their Preparation, Structures, and Synthetic Applicability

V. D. Filimonov, M. Trusova, P. Postnikov, E. A. Krasnokutskaya, Y. M. Lee, H. Y. Hwang, H. Kim, K.-W. Chi, Org. Lett., 2008, 10, 3961-3964.

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Key Words

iodoarenes, aromatic amines, diazotization, Sandmeyer reaction, potassium iodide, sodium nitrite, cation-exchange resin

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ID: J66-Y2008-0030