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C-F bond substitution via aziridinium ion intermediates

Journal article
Authors Annika M. Träff
Mario Janjetovic
Göran Hilmersson
Published in Chemical Communications
Volume 51
Issue 68
Pages 13260-13263
ISSN 1359-7345
Publication year 2015
Published at Department of Chemistry and Molecular Biology
Pages 13260-13263
Language en
Links dx.doi.org/10.1039/c5cc04723d
Keywords RING-OPENING REACTIONS, PALLADIUM-CATALYZED SUBSTITUTION, FRIEDEL-CRAFTS, REACTION, ALKYL FLUORIDES, PHOTOREDOX CATALYSIS, SELECTIVE ACTIVATION, AMMONIUM-IONS, FLUORINATION, MILD, AMINOFLUORINATION, Chemistry, Multidisciplinary
Subject categories Chemical Sciences

Abstract

Aliphatic 1,2-aminofluorides undergo extremely fast substitution reactions under the influence of lanthanum tris(hexamethyldisilazide). The substitution proceeds via an in situ generated aziridinium ion intermediate, which subsequently undergoes ring opening by addition of a nucleophile, yielding various beta-substituted amines.

Page Manager: Webmaster|Last update: 9/11/2012
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