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Org Lett. 2008 Sep 18;10(18):3961-4. doi: 10.1021/ol8013528. Epub 2008 Aug 23.

Unusually stable, versatile, and pure arenediazonium tosylates: their preparation, structures, and synthetic applicability.

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1
Department of Organic Chemistry, Tomsk Polytechnic University, Tomsk 634050 Russia. filimonov@tpu.ru

Abstract

A new, simple, and effective method for the diazotization of a wide range of arylamines has been developed by using a polymer-supported diazotization agent in the presence of p-toluenesulfonic acid. Various pure arenediazonium tosylates with unusual stabilities can be easily prepared by this method. As a result, these salts are useful and versatile substrates for subsequent transformations, such as halogenation and Heck-type reactions. The unusual stabilities of arenediazonium tosylates are also preliminarily discussed with their X-ray structures.

PMID:
18722457
DOI:
10.1021/ol8013528
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