A Simple and Effective Synthesis of Aryl Azides via Arenediazonium Tosylates

Ksenia V. Kutonova, Marina E. Trusova, Pavel S. Postnikov, Victor D. Filimonov*, Joseph Parello*

*National Research Tomsk Polytechnic University, 634050 Tomsk, Russian Federation; Vanderbilt University, Nashville, TN 37232, USA, Email: filimonovtpu.ru, joseph.parellovanderbilt.edu

K. V. Kutonova, M. E. Trusova, P. S. Postnikov, V. D. Filimonov, J. Parello, Synthesis, 2013, 45, 2706-2710.

DOI: 10.1055/s-0033-1339648

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Abstract

Aromatic azides are formed in high yield from arenediazonium tosylates and sodium azide in water at room temperature. An in situ diazotization followed by azidation in the presence of p-TsOH allows the direct transformation of aromatic amines. Besides being experimentally simple, these methods do not require any metal catalysis and provide clean products without purification.

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

diazotization, sodium azide, aromatic amines, aryl azides, p-TsOH, aqueous medium

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ID: J66-Y2013