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Synthesis 2010(14): 2490-2494  
DOI: 10.1055/s-0029-1218816
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© Georg Thieme Verlag Stuttgart ˙ New York

Large-Scale Preparation of Aromatic Fluorides via Electrophilic Fluorination with Functionalized Aryl- or Heteroarylmagnesium Reagents

Shigeyuki Yamada, Paul Knochel*
Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5-13, Haus F, 81377 München, Germany
Fax: +49(89)218077680; e-Mail: paul.knochel@cup.uni-muenchen.de;
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Publication History

Received 20 April 2010
Publication Date:
15 June 2010 (online)

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Abstract

Functionalized aryl- or heteroarylmagnesium reagents, prepared from the corresponding bromides or iodides using halogen-magnesium exchange or direct magnesium insertion in the presence of lithium chloride, reacted smoothly with N-fluorobenzenesulfon­imide, (PhSO2)2NF, in the mixed solvent (4:1 CH2Cl2-perfluorodecalin) to give the corresponding aromatic fluorides in moderate to good yields.

Key words

arenes - electrophilic substitution - fluorination - Grignard reagents - heteroaromatic compounds

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