ZrCl4-promoted halogen migration during an electrophilic amination of halogenated phenols

Sergeja Bombek; Roman Lenaršič; Marijan Kočevar; Laurent Saint-Jalmes; Jean-Roger Desmurs; Slovenko Polanc

doi:10.1039/B203622C

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ZrCl₄-promoted halogen migration during an electrophilic amination of halogenated phenols†‡

Sergeja Bombek,^a Roman Lenaršič,^b Marijan Kočevar,^a Laurent Saint-Jalmes,^c Jean-Roger Desmurs^d and Slovenko Polanc*^a

Author affiliations

* Corresponding authors

^a Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, SI-1000, Ljubljana, Slovenia
E-mail: slovenko.polanc@uni-lj.si

^b KRKA, d.d, Novo mesto, Šmarješka 6, SI-8000, Novo mesto, Slovenia

^c Rhodia—Centre de Recherches de Lyon, 85, av. Freres Perret, 69192, Saint Fons Cedex, France

^d Rhodia, Pharmaceutical Ingredients Etoile Part-Dieu, 190, av. Thiers, 69457, Lyon Cedex 06, France

Abstract

An electrophilic amination of halogenated phenols with diisopropyl diazenedicarboxylate in the presence of ZrCl₄ as a Lewis acid, accompanied by a halogen migration, was demonstrated for the first time; the fluorine, chlorine, bromine, or iodine atom migrated during the amination process under mild reaction conditions.

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Supplementary files

Spectroscopic data, mp and elemental analysis (or HRMS) for the products 3 and 4 DOC (37K)

Article information

DOI: https://doi.org/10.1039/B203622C
Article type: Communication
Submitted: 15 Apr 2002
Accepted: 27 May 2002
First published: 12 Jun 2002

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Chem. Commun., 2002, 1494-1495

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ZrCl₄-promoted halogen migration during an electrophilic amination of halogenated phenols

S. Bombek, R. Lenaršič, M. Kočevar, L. Saint-Jalmes, J. Desmurs and S. Polanc, Chem. Commun., 2002, 1494 DOI: 10.1039/B203622C

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