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Synthesis 2010(14): 2490-2494
DOI: 10.1055/s-0029-1218816
DOI: 10.1055/s-0029-1218816
PSP
© Georg Thieme Verlag
Stuttgart ˙ New York
Large-Scale Preparation of Aromatic Fluorides via Electrophilic Fluorination with Functionalized Aryl- or Heteroarylmagnesium Reagents
Further Information
Received
20 April 2010
Publication Date:
15 June 2010 (online)
Publication History
Publication Date:
15 June 2010 (online)
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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