Issue 68, 2015
From the journal:

Chemical Communications

C–F bond substitution via aziridinium ion intermediates†

A. M. Träff,a   M. Janjetovica  and  G. Hilmersson*a  

* Corresponding authors

a Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, Gothenburg, Sweden
E-mail: hilmer@chem.gu.se
Tel: +46-317869022

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 β-substituted amines.

Graphical abstract: C–F bond substitution via aziridinium ion intermediates

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Article information

DOI
https://doi.org/10.1039/C5CC04723D
Article type
Communication
Submitted
08 Jun 2015
Accepted
14 Jul 2015
First published
15 Jul 2015

Chem. Commun., 2015,51, 13260-13263

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C–F bond substitution via aziridinium ion intermediates

A. M. Träff, M. Janjetovic and G. Hilmersson, Chem. Commun., 2015, 51, 13260 DOI: 10.1039/C5CC04723D

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