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

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...

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Bibliographic Details
Published inChemical communications (Cambridge, England) no. 14; pp. 1494 - 1495
Main Authors Bombek, S, Lenarsic, R, Kocevar, M, Saint-Jalmes, L, Desmurs, Polanc, S
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2002
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
FUNCTIONALIZATION
MECHANISM
DANCE REACTION
1ST METALATION
ISOMERIZATION
DIAZINES
INTERMEDIATE
ARYL IODIDES
RICH ARENES
DIRECTED ORTHO-LITHIATION
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/b203622c