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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, Email:

S. Yamada, P. Knochel, Synthesis, 2010, 2490-2494.

DOI: 10.1055/s-0029-1218816

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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 to give the corresponding aromatic fluorides in good yields.

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Key Words

arenes, electrophilic substitution, fluorination, Grignard reagents, heteroaromatic compounds, NFSI

ID: J66-Y2010-1990