Organic Chemistry Portal

Abstracts

Search:

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

Victor D. Filimonov*, Marina Trusova, Pavel Postnikov, Elena A. Krasnokutskaya, Young Min Lee, Ho Yun Hwang, Hyunuk Kim and Ki-Whan Chi

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

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.

DOI: 10.1021/ol8013528 (free Supporting Information)


see article for more examples

Abstract

A new, simple, and effective method for the diazotization of a wide range of arylamines using a polymer-supported diazotization agent in the presence of p-toluenesulfonic acid gives various pure arenediazonium tosylates with unusual high stabilities. As a result, these salts are useful and versatile substrates for subsequent transformations, such as halogenation and Heck-type reactions.

see article for more examples



A Simple and Effective Synthesis of Aryl Azides via Arenediazonium Tosylates

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

Sulfonic Acid Based Cation-Exchange Resin: A Novel Proton Source for One-Pot Diazotization-Iodination of Aromatic Amines in Water

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


Key Words

Diazotization, Arenediazonium Salts, Sandmeyer Reaction


ID: J54-Y2008-2530